Research progress on radical carbonylation of alkanes or alkylarenes with carbon monoxide

SUN Qiao; YIN Aihua; XU Yuan; SUI Shanhong; DONG Yan; WANG Changsheng; ZHANG Dongshun; GUO Kai

doi:10.12434/j.issn.2097-2547.20240312

您当前的位置：

首页 >

文章列表页 >

Research progress on radical carbonylation of alkanes or alkylarenes with carbon monoxide

更新时间：2025-04-27

- Research progress on radical carbonylation of alkanes or alkylarenes with carbon monoxide
- Vol. 50, Issue 4, Pages: 1-18(2025)
- 作者机构：
  
  1.南京工业大学食品与轻工学院，江苏南京 211816
  2.南京工业大学生物与制药工程学院，江苏南京 211816
  3.南洋理工大学化学化工与生物技术学院，新加坡 637371
  4.中石化（北京）化工研究院，北京 100013
- 作者简介：
- 基金信息：
- DOI：10.12434/j.issn.2097-2547.20240312
  CLC： TQ216;O622.5
- Received：25 July 2024，
  
  Revised：2024-08-21，
  
  Published：25 April 2025
- 稿件说明：
移动端阅览
孙巧,殷爱华,徐元等.烷烃/烷基芳烃与一氧化碳的自由基羰基化研究进展[J].低碳化学与化工,2025,50(04):1-18.

SUN Qiao,YIN Aihua,XU Yuan,et al.Research progress on radical carbonylation of alkanes or alkylarenes with carbon monoxide[J].Low-Carbon Chemistry and Chemical Engineering,2025,50(04):1-18.
孙巧,殷爱华,徐元等.烷烃/烷基芳烃与一氧化碳的自由基羰基化研究进展[J].低碳化学与化工,2025,50(04):1-18. DOI： 10.12434/j.issn.2097-2547.20240312.

SUN Qiao,YIN Aihua,XU Yuan,et al.Research progress on radical carbonylation of alkanes or alkylarenes with carbon monoxide[J].Low-Carbon Chemistry and Chemical Engineering,2025,50(04):1-18. DOI： 10.12434/j.issn.2097-2547.20240312.

摘要

羰基官能团广泛存在于天然产物、医药、农药和高分子材料结构中，开发新颖、高效以及绿色的羰基化方法是合成化学领域最热门的研究课题之一。烷烃和烷基芳烃作为重要的能源和化工原料，广泛存在于石油和天然气中。从简单烷烃（如环戊烷、环己烷）或烷基芳烃（如甲苯、乙苯）出发，通过C—H键的直接羰基化高选择性地制备高附加值羰基衍生物是一个充满挑战且富有前景的研究领域。在众多羰基供体中，一氧化碳（CO）因具有原子效率100%和价格低廉的优点，是使用最为广泛的羰基化试剂。基于过去近15年来烷烃、烷基芳烃与CO的自由基羰基化领域取得的重要成果，综述了以过氧类化合物或光催化剂作为引发剂，H

O、H

、醇、芳基亚磺酸酯、偶氮二羧酸酯、胺、亚胺、酰胺和烯烃等作为反应试剂，制备羧酸、酯、酰胺类（包括酰肼、酰胺、

-酮酰胺、

-内酰胺和酰亚胺）和酮类（包括手性胺基酮）高附加值羰基衍生物的研究进展。然后，根据羰基化反应的产物类型进行了分类阐述，并对反应的底物适用范围以及典型的反应机理进行了讨论。最后，对烷烃和烷基芳烃自由基羰基化领域所面临的挑战和机遇进行了分析和展望。

Abstract

Carbonyl functional groups are widely present in the structures of natural products

pharmaceuticals

agrochemicals

and polymer materials. The development of innovative

efficient and green carbonylation methods is one of the hottest research topics in the field of synthetic chemistry. As important energies and chemical raw materials

alkanes and alkylarenes are widely prevalent in petroleum and natural gas. The highly selective preparation of high value-added carbonyl derivatives through direct carbonylation of C—H bonds

starting from simple alkanes (e.g.

cyclopentane

cyclohexane) or alkylarenes (e.g.

toluene

ethylbenzene)

represents a challenging and promising research area. Among the diverse carbonyl donors

carbon monoxide (CO) is the most extensively utilized carbonylation reagent owing to its 100% atomic efficiency and cost-effectiveness. Based on the significant achievements in the field of radical carbonylation of alkanes or alkylarenes with carbon monoxide over the past fifteen years

the progress on the synthesis of high value-added carbonyl derivatives such as acids

esters

amides (including acyl hydrazides

amides

-ketoamides

-lactams and imides) and ketones (including chiral amino ketones) by utilizing peroxide-type compounds or photocatalysts as the initiators

and H

alcohols

arylsulfinates

azodicarboxylates

amines

imines

amides or olefins as the reaction partners was summarized. Then

the product types of carbonylation reactions were classified and explained

and the substrate scopes and typical reaction mechanisms were discussed. Finally

the challenges and opportunities in the field of radical carbonylation of alkanes and alkylarenes were analyzed and prospected.

关键词

Keywords

references

BARNARD C F J . Palladium-catalyzed carbonylation—A reaction come of age [J ] . Organometallics , 2008 , 27 ( 21 ): 5402 - 5422 .

BRENNFÜHRER A , NEUMANN H , BELLER M . Palladium-catalyzed carbonylation reactions of aryl halides and related compounds [J ] . Angewandte Chemie International Edition , 2009 , 48 ( 23 ): 4114 - 4133 .

SUMINO S , FUSANO A , FUKUYAMA T , et al . Carbonylation reactions of alkyl iodides through the interplay of carbon radicals and Pd catalysts [J ] . Accounts of Chemical Research , 2014 , 47 ( 5 ): 1563 - 1574 .

WU X F . Palladium-catalyzed carbonylative transformation of aryl chlorides and aryl tosylates [J ] . RSC Advances , 2016 , 6 ( 87 ): 83831 - 83837 .

王鹏 , 史会兵 , 赵德明 , 等 . 过渡金属催化氯代物的羰基化反应研究进展 [J ] . 化工进展 , 2023 , 42 ( 9 ): 4649 - 4666 .

WANG P , SHI H B , ZHAO D M , el al . Recent advances on transition metal catalyzed carbonylation of chlorinated compounds [J ] . Chemical Industry and Engineering Progress , 2023 , 42 ( 9 ): 4649 - 4666 .

LIU Q , ZHANG H , LEI A W . Oxidative carbonylation reactions: Organometallic compounds (R—M) or hydrocarbons (R—H) as nucleophiles [J ] . Angewandte Chemie International Edition , 2011 , 50 ( 46 ): 10788 - 10799 .

GADGE S T , GAUTAM P , BHANAGE B M . Transition metal-catalyzed carbonylative C—H bond functionalization of arenes and C(sp 3 )—H bond of alkanes [J ] . The Chemical Record , 2016 , 16 ( 2 ): 835 - 856 .

ZHU C , LIU J , LI M B , et al . Palladium-catalyzed oxidative dehydrogenative carbonylation reactions using carbon monoxide and mechanistic overviews [J ] . Chemical Society Reviews , 2020 , 49 ( 2 ): 341 - 353 .

武泽臣 , 程沧 , 张扬会 . 过渡金属催化的碳氢键与一氧化碳的反应 [J ] . 有机化学 , 2021 , 41 ( 6 ): 2155 - 2174 .

WU Z C , CHENG C , ZHANG Y . Transition metal-catalyzed reactions of C—H bonds with carbon monoxide [J ] . Chinese Journal of Organic Chemistry , 2021 , 41 ( 6 ): 2155 - 2174 .

LIU Y , CHEN Y H , YI H , et al . An update on oxidative C—H carbonylation with CO [J ] . ACS Catalysis , 2022 , 12 ( 13 ): 7470 - 7485 .

PENG J B , GENG H Q , WU X F . The chemistry of CO: Carbonylation [J ] . Chem , 2019 , 5 ( 3 ): 526 - 552 .

AKHREM I S , AFANAS’EVA L V , VITT S V , et al . First examples of the selective carbonylation of C 6 ~C 10 linear alkanes to tertiary carbonyl-containing compounds [J ] . Mendeleev Communications , 2002 , 12 ( 5 ): 180 - 182 .

LI S , CHEN G , FENG C G , et al . Ligand-enabled γ -C—H olefination and carbonylation: Construction of β -quaternary carbon centers [J ] . Journal of the American Chemical Society , 2014 , 136 ( 14 ): 5267 - 5270 .

HASEGAWA N , CHARRA V , INOUE S , et al . Highly regioselective carbonylation of unactivated C(sp 3 )—H bonds by ruthenium carbonyl [J ] . Journal of the American Chemical Society , 2011 , 133 ( 21 ): 8070 - 8073 .

YOO E J , WASA M , YU J Q . Pd(II)-catalyzed carbonylation of C(sp 3 )—H bonds: A new entry to 1,4-dicarbonyl compounds [J ] . Journal of the American Chemical Society , 2010 , 132 ( 49 ): 17378 - 17380 .

BANERJEE A , SARKAR S , PATEL B K . C—H functionalisation of cycloalkanes [J ] . Organic & Biomolecular Chemistry , 2017 , 15 ( 3 ): 505 - 530 .

王长城 , 刘峰 , 施章杰 . 低碳烷烃均相转化研究进展 [J ] . 中国科学: 化学 , 2020 , 50 ( 7 ): 756 - 765 .

WANG C C , LIU F , SHI Z J . Homogeneous functionalization of light alkanes [J ] . SCIENTIA SINICA Chimica , 2020 , 50 ( 7 ): 756 - 765 .

PULCINELLA A , MAZZARELLA D , NOËL T . Homogeneous catalytic C(sp 3 )—H functionalization of gaseous alkanes [J ] . Chemical Communications , 2021 , 57 ( 78 ): 9956 - 9967 .

VELASCO-RUBIO Á , MARTÍNEZ-BALART P , ÁLVAREZ-CONSTANTINO A M , et al . C—C bond formation via photocatalytic direct functionalization of simple alkanes [J ] . Chemical Communications , 2023 , 59 ( 62 ): 9424 - 9444 .

CHANG L , WANG S , AN Q , et al . Resurgence and advancement of photochemical hydrogen atom transfer processes in selective alkane functionalizations [J ] . Chemical Science , 2023 , 14 ( 25 ): 6841 - 6859 .

SAKAKURA T , TANAKA M . Efficient catalytic C—H activation of alkanes: Regioselective carbonylation of the terminal methyl group of n -pentane by RhCl(CO)(PMe 3 ) 2 [J ] . Journal of the Chemical Society , Chemical Communications, 1987 , 10 : 758 - 759 .

AKHREM I . Selective and effective functionalization of alkanes and cycloalkanes with CO by polyhalomethanes combined with aluminum halides in organic media [J ] . Topics in Catalysis , 1998 , 6 ( 1 ): 27 - 39 .

OSHITA M , CHATANI N . Efficient synthesis of 1-adamantanecarboxaldehyde by the GaCl 3 -mediated carbonylation of adamantane under mild reaction conditions [J ] . Organic Letters , 2004 , 6 ( 23 ): 4323 - 4325 .

FERGUSON R R , CRABTREE R H . Mercury-photosensitized sulfination, hydrosulfination, and carbonylation of hydrocarbons: Alkane and alkene conversion to sulfonic acids, ketones, and aldehydes [J ] . The Journal of Organic Chemistry , 1991 , 56 ( 19 ): 5503 - 5510 .

BOESE W T , GOLDMAN A S . Photochemical cyclohexane carbonylation cocatalyzed by d8 transition metal carbonyls and aromatic ketones and aldehydes [J ] . Journal of the American Chemical Society , 1992 , 114 ( 1 ): 350 - 351 .

BOESE W T , GOLDMAN A S . Alkane carbonylation photocatalyzed by aromatic ketones under high CO pressure [J ] . Tetrahedron Letters , 1992 , 33 ( 16 ): 2119 - 2122 .

JAYNES B S , HILL C L . Radical carbonylation of alkanes via polyoxotungstate photocatalysis [J ] . Journal of the American Chemical Society , 1995 , 117 ( 16 ): 4704 - 4705 .

CHOI J C , KOBAYASHI Y , SAKAKURA T . C—H bond activation in dense carbon dioxide: Rhodium-catalyzed methane carbonylation and alkane dehydrogenation [J ] . The Journal of Organic Chemistry , 2001 , 66 ( 15 ): 5262 - 5263 .

SAKAKURA T , ISHIGURO K , OKANO M , et al . Homogeneous catalysis in liquefied gas. Complex-catalyzed selective and direct conversion of propane to butanal at room temperature [J ] . Chemistry Letters , 2005 , 26 ( 11 ): 1089 - 1090 .

FUJIWARA Y , TAKAKI K , WATANABE J , et al . Thermal activation of alkane C—H bonds by palladium catalysts. carbonylation of alkanes with carbon monoxide [J ] . Chemistry Letters , 1989 , 18 ( 9 ): 1687 - 1688 .

NAKATA K , YAMAOKA Y , MIYATA T , et al . Palladium(II) and/or copper(II)-catalyzed carboxylation of small alkanes such as methane and ethane with carbon monoxide [J ] . Journal of Organometallic Chemistry , 1994 , 473 ( 1 ): 329 - 334 .

FUJIWARA Y , TABAKI K , TANIGUCHI Y . Exploitation of synthetic reactions via C—H bond activation by transition metal catalysts. Carboxylation and aminomethylation of alkanes or arenes [J ] . Synlett , 1996 , ( 7 ): 591 - 599 .

ASADULLAH M , TANIGUCHI Y , KITAMURA T , et al . Cobalt catalyzed carboxylation reaction of saturated hydrocarbons with CO in the presence of K 2 S 2 O 8 and TFA under mild conditions [J ] . Tetrahedron Letters , 1999 , 40 ( 50 ): 8867 - 8871 .

TANIGUCHI Y , HAYASHIDA T , SHIBASAKI H , et al . Highly efficient vanadium-catalyzed transformation of CH 4 and CO to acetic acid [J ] . Organic Letters , 1999 , 1 ( 4 ): 557 - 560 .

KIRILLOVA M V , KIRILLOV A M , POMBEIRO A J L . Metal-free and copper-promoted single-pot hydrocarboxylation of cycloalkanes to carboxylic acids in aqueous medium [J ] . Advanced Synthesis & Catalysis , 2009 , 351 ( 17 ): 2936 - 2948 .

KIRILLOVA M V , KIRILLOV A M , KUZNETSOV M L , et al . Alkanes to carboxylic acids in aqueous medium: Metal-free and metal-promoted highly efficient and mild conversions [J ] . Chemical Communications , 2009 , 17 : 2353 - 2355 .

KIRILLOVA M V , KIRILLOV A M , POMBEIRO A J L . Mild, single-pot hydrocarboxylation of gaseous alkanes to carboxylic acids in metal-free and copper-promoted aqueous systems [J ] . Chemistry—A European Journal , 2010 , 16 ( 31 ): 9485 - 9493 .

KIRILLOV A M , KIRILLOVA M V , POMBEIRO A J L . Multicopper complexes and coordination polymers for mild oxidative functionalization of alkanes [J ] . Coordination Chemistry Reviews , 2012 , 256 ( 23 ): 2741 - 2759 .

SUTRADHAR M , KIRILLOVA M V , DA SILVA M F C , et al . Tautomeric effect of hydrazone schiff bases in tetranuclear Cu(II) complexes: Magnetism and catalytic activity towards mild hydrocarboxylation of alkanes [J ] . Dalton Transactions , 2013 , 42 ( 47 ): 16578 - 16587 .

KIRILLOVA M V , FERNANDES T A , ANDRÉ V , et al . Mild C—H functionalization of alkanes catalyzed by bioinspired copper(II) cores [J ] . Organic & Biomolecular Chemistry , 2019 , 17 ( 33 ): 7706 - 7714 .

PAUL A , RIBEIRO A P C , KARMAKAR A , et al . A Cu(II) MOF with a flexible bifunctionalised terpyridine as an efficient catalyst for the single-pot hydrocarboxylation of cyclohexane to carboxylic acid in water/ionic liquid medium [J ] . Dalton Transactions , 2016 , 45 ( 32 ): 12779 - 12789 .

RIBEIRO A P C , MARTINS L M D R S , CARABINEIRO S A C , et al . Gold nanoparticles deposited on surface modified carbon xerogels as reusable catalysts for cyclohexane C—H activation in the presence of CO and water [J ] . Molecules , 2017 , 22 ( 4 ): 603 .

RIBEIRO A P C , MARTINS L M D R S , CARABINEIRO S A C , et al . Gold nanoparticles deposited on surface modified carbon materials as reusable catalysts for hydrocarboxylation of cyclohexane [J ] . Applied Catalysis A: General , 2017 , 547 : 124 - 131 .

PAKRIEVA E , RIBEIRO A P C , MARTINS L M D R S , et al . Commercial gold(III) complex supported on functionalized carbon materials as catalyst for cyclohexane hydrocarboxylation [J ] . Catalysis Today , 2020 , 357 : 39 - 45 .

MATIAS I A S , RIBEIRO A P C , ALEGRIA E C B A , et al . C-scorpionate iron(II) complexes as highly selective catalysts for the hydrocarboxylation of cyclohexane [J ] . Inorganica Chimica Acta , 2019 , 489 : 269 - 274 .

RAYMENANTS F , MASSON T M , SANJOSÉ-ORDUNA J , et al . Efficient C(sp 3 )—H carbonylation of light and h eavy hydrocarbons with carbon monoxide via hydrogen atom transfer photocatalysis in flow [J ] . Angewandte Chemie International Edition , 2023 , 62 ( 36 ): e202308563 .

GUNSALUS N J , KOPPAKA A , PARK S H , et al . Homogeneous functionalization of methane [J ] . Chemical Reviews , 2017 , 117 ( 13 ): 8521 - 8573 .

申志兵 , 付娆 , 唐瑞源 , 等 . 甲烷低温活化机理及其参与的化学反应研究进展 [J ] . 低碳化学与化工 , 2023 , 48 ( 4 ): 1 - 7 .

SHEN Z B , FU R , TANG R Y , et al . Research progress on low temperature activation mechanism of methane and its involved chemical reactions [J ] . Low-Carbon Chemistry and Chemical Engineering , 2023 , 48 ( 4 ): 1 - 7 .

余海杰 , 李潇 , 冉建速 , 等 . 甲烷选择性氧化制含氧化合物催化剂研究进展 [J ] . 低碳化学与化工 , 2023 , 48 ( 5 ): 9 - 21 .

YU H J , LI X , RAN J S , et al . Research progress in catalysts for selective oxidation of methane to oxygenated compounds [J ] . Low-Carbon Chemistry and Chemical Engineering , 2023 , 48 ( 5 ): 9 - 21 .

EZHOVA N N , KOLESNICHENKO N V , MAXIMOV A L . Modern methods for producing acetic acid from methane: New trends (a review) [J ] . Petroleum Chemistry , 2022 , 62 : 40 - 61 .

LIN M , SEN A . Direct catalytic conversion of methane to acetic acid in an aqeous medium [J ] . Nature , 1994 , 368 : 613 - 615 .

NARSIMHAN K , MICHAELIS V K , MATHIES G , et al . Methane to acetic acid over Cu-exchanged zeolites: Mechanistic insights from a site-specific carbonylation reaction [J ] . Journal of the American Chemical Society , 2015 , 137 ( 5 ): 1825 - 1832 .

SHAN J J , LI M W , ALLARD L F , et al . Mild oxidation of methane to methanol or acetic acid on supported isolated rhodium catalysts [J ] . Nature , 2017 , 551 : 605 - 608 .

TANG Y , LI Y T , FUNG V , et al . Single rhodum atoms anchored in micropores for effiecient transformation of methane under mild conditions [J ] . Nature Communications , 2018 , 9 : 1231 .

WU B , LIN T J , LU Z X , et al . Fe binuclear sites convert methane to acetic acid with ultrahigh selectivity [J ] . Chem , 2022 , 8 ( 6 ): 1658 - 1672 .

CHENG Q P , YAO X L , LI G N , et al . Atomically dispersed iron-copper dual-metal sites synergistically boost carbonylation of methane [J ] . Angewandte Chemie International Edition , 2024 , 63 ( 43 ): e202411048 .

WANG C W , SUN Y , WANG L J , et al . Oxidative carbonylation of methane to acetic acid on an Fe-modified ZSM-5 zeolite [J ] . Applied Catalysis B: Environmental , 2023 , 329 : 122549 .

DONG C Y , MARINOVA M , TAYEB K B , et al . Direct photocatalytic synthesis of acetic acid from methane and CO at ambient temperature using water as oxidant [J ] . Journal of the American Chemical Society , 2023 , 145 ( 2 ): 1185 - 1193 .

KOHLPAINTNER C W , BELLER M . Palladium-catalyzed carbonylation of benzyl chlorides to phenylacetic acids—A new two-phase process [J ] . Journal of Molecular Catalysis A: Chemical , 1997 , 116 ( 1-2 ): 259 - 267 .

JONES R V H , LINDSELL W E , PALMER D D , et al . Palladium-catalyzed carbonylation of arylmethyl halides: Efficient synthesis of arylacetic acid and esters [J ] . Tetrahedron Letters , 2005 , 46 ( 50 ), 8695 - 8697 .

LAPIDUS A L , ELISEEV O L , BONDARENKO T N , et al . Exceptionally simple catalytic system for the carbonylation of benzyl halides [J ] . Mendeleev Communications , 2009 , 19 ( 5 ): 256 - 257 .

DING Y Z , HUANG R B , ZHANG W , et al . Nickel-catalyzed oxidative carbonylation of alkylarenes to arylacetic acids [J ] . Organic Letters , 2022 , 24 ( 43 ): 7972 - 7977 .

XIE P , XIE Y J , QIAN B , et al . Palladium-catalyzed oxidative carbonylation of benzylic C—H bonds via nondirected C(sp 3 )—H activation [J ] . Journal of the American Chemical Society , 2012 , 134 ( 24 ): 9902 - 9905 .

LU L J , SHI R Y , LIU L Y , et al . Oxidative alkane C—H alkoxycarbonylation [J ] . Chemistry—A European Journal , 2016 , 22 ( 41 ): 14484 - 14488 .

XIONG Q , XU D D , SHAN C H , et al . Investigating the mechanism of palladium-catalyzed radical oxidative C(sp 3 )—H carbonylation: A DF T study [J ] . Chemistry—An Asian Journal , 2019 , 14 ( 5 ): 655 - 661 .

LI Y H , WANG C S , ZHU F X , et al . Copper-catalyzed alkoxycarbonylation of alkanes with alcohols [J ] . ChemSusChem , 2017 , 10 ( 7 ): 1341 - 1345 .

LU L J , CHENG D Y , ZHAN Y F , et al . Metal-free radical oxidative alkoxycarbonylation and imidation of alkanes [J ] . Chemical Communications , 2017 , 53 ( 51 ): 6852 - 6855 .

XIAO W J , VASAPOLLO G , ALPER H . Highly regioselective palladium-catalyzed thiocarbonylation of allenes with thiols and carbon monoxide [J ] . Journal of the Organic Chemistry , 1998 , 63 ( 8 ): 2609 - 2612 .

HIRSCHBECK V , GEHRTZ P H , FLEISCHER I . Regioselective thiocarbonylation of vinyl arenes [J ] . Journal of the American Chemical Society , 2016 , 138 ( 51 ): 16794 - 16799 .

AI H J , ZHAO F Q , GENG H Q , et al . Palladium-catalyzed thiocarbonylation of alkenes toward linear thioesters [J ] . ACS Catalysis , 2021 , 11 ( 6 ): 3614 - 3619 .

CAI S Z , YU R R , LI C , et al . Nickel-catalyzed enantioselective hydrothiocarbonylation of cyclopropenes [J ] . Organic Letters , 2023 , 25 ( 48 ): 8683 - 8687 .

LI Y H , ZHU F X , WANG Z C , et al . Synthesis of thioethers and thioesters with alkyl arylsulfinates as the sulfenylation agent under metal-free conditions [J ] . Chemistry—An Asian Journal , 2016 , 11 ( 24 ): 3503 - 3507 .

RYU I , TANI A , FUKUYAMA T , et al . Efficient C—H/C—N and C—H/C—CO—N conversion via decatungstate-photoinduced alkylation of diisopropyl azodicarboxylate [J ] . Organic Letters , 2013 , 15 ( 10 ): 2554 - 2557 .

XIE P , XIA C G , HUANG H M . Palladium-catalyzed oxidative aminocarbonylation: A new entry to amides via C—H activation [J ] . Organic Letters , 2013 , 15 ( 13 ): 3370 - 3373 .

LIU H Z , LAURENCZY G , YAN N , et al . Amide bond formation via C(sp 3 )—H bond functionalization and CO insertion [J ] . Chemical Communications , 2014 , 50 ( 3 ): 341 - 343 .

LI Y H , ZHU F X , WANG Z C , et al . Copper-catalyzed carbonylative synthesis of aliphatic amides from alkanes and primary amines via C(sp 3 )—H bond activation [J ] . ACS Catalysis , 2016 , 6 ( 8 ): 5561 - 5564 .

LU L J , PEI X L , MEI Y , et al . Carbon nanofibrous microspheres promote the oxidative double carbonylation of alkanes with CO [J ] . Chem , 2018 , 4 ( 12 ): 2861 - 2871 .

LU L J , QIU F Y , ALHUMADE H , et al . Tuning the oxidative mono- or double-carbonylation of alkanes with CO by choosing a Co or Cu catalyst [J ] . ACS Catalysis , 2022 , 12 ( 15 ): 9664 - 9669 .

DING Y Z , WU J N , HUANG H M . Carbonylative formal cycloaddition between alkylarenes and aldimines enabled by palladium-catalyzed double C—H bond activation [J ] . Journal of the American Chemical Society , 2023 , 145 ( 9 ): 4982 - 4988 .

LI Y H , DONG K W , ZHU F X , et al . Copper-catalyzed carbonylative coupling of cycloalkanes and amides [J ] . Angewandte Chemie International Edition , 2016 , 55 ( 25 ): 7227 - 7230 .

ZHANG H , DAI C W , LIU L C , et al . Nickel(II)-catalyzed efficient aminocarbonylation of unreactive alkanes with formanilides—Exploiting the deformylation behavior of imides [J ] . Tetrahedron , 2018 , 74 ( 27 ): 3712 - 3718 .

UENOYAMA Y , FUKUYAMA T , MORIMOTO K , et al . Trifluoromethyl-radical-mediated carbonylation of alkanes leading to ethynyl ketones [J ] . Helvetica Chimica Acta , 2006 , 89 ( 10 ): 2483 - 2494 .

RYU I , TANI A , FUKUYAMA T , et al . Atom-economical synthesis of unsymmetrical ketones through photocatalyzed C—H activation of alkanes and coupling with CO and electrophilic alkenes [J ] . Angewandte Chemie International Edition , 2011 , 50 ( 8 ): 1869 - 1872 .

CHEN L , HOU J , ZHENG M , et al . Carbonylative coupling of simple alkanes and alkenes enabled by organic photoredox catalysis [J ] . Chemical Communications , 2021 , 57 ( 79 ): 10210 - 10213 .

DING W W , HE Z Y , SAYED M , et al . Enantioselective synthesis of β - and α -amino ketones through reversible alkane ca rbonylation [J ] . Nature Synthesis , 2024 , 3 ( 4 ): 507 - 516 .

Views

230

下载量

CNKI被引量

Alert me when the article has been cited

提交

Tools

Publicity Resources

Inhibition effect of CO₂ and CO on hydrogen permeation in palladium membrane

Observation and evidence of compensation effect in syngas conversion reaction

Study of phenyacetic acid synthesis by carbonylation

Purification and recovering of CO from yellow phosphorus tail-gas by TSA and PSA

Related Author

SUI Shanhong

DONG Yan

ZHANG Dongshun

ZHAO Hang

LIU Xue

CAO Daofan

LI Chao

JIANG Fenghao

Related Institution

SINOPEC Beijing Research Institute of Chemical Industry

Department of Chemistry, Southern University of Science and Technology

Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology

College of Innovation and Entrepreneurship, Southern University of Science and Technology

School of Chemistry and Chemical Engineering, Harbin Institute of Technology

Postal code：610225
Tel：028-85964717 Email：236764603@qq.com
Technical support is provided by Beijing Founder electronics co., LTD 蜀ICP备12008600号-10 蜀公网安备51012202001533
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.
Total Visits：408680 Visits Today：717

⁰