Rh-Catalyzed General Method for Directed C-H Functionalization via Decarbonylation of in-Situ-Generated Acid Fluorides from Carboxylic Acids

被引：10

作者：

He, Bangyue ^{[1
,2
]}

Liu, Xiaojie ^{[1
]}

Li, Hongyi ^{[1
]}

Zhang, Xiaofeng ^{[1
]}

Ren, Yuxi ^{[1
]}

Su, Weiping ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Ctr Excellence Mol Synth, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Fuzhou 350002, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 11期

基金：

中国国家自然科学基金;

关键词：

DECARBOXYLATION; ALKYLATION; ACTIVATION; ARYLATION; AMIDES; BONDS;

D O I：

10.1021/acs.orglett.1c01103

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Rh-catalyzed decarbonylative C-H coupling of in-situ-generated acid fluorides with amide substrates bearing ortho-Csp(2)-H bonds has been developed. This method enables alkyl, aryl, and alkenyl carboxylic acids to undergo decarbonylative coupling with C-H bonds of (hetero)aromatic or alkenyl amides in generally good yields via the in situ conversion of carboxylic acids into acid fluorides and also allows for the functionalization of a series of structurally complex carboxyl-containing natural products and pharmaceuticals as well as pharmaceutical amide derivatives.

引用

页码：4191 / 4196

页数：6

共 36 条

[31] Synthetic approach of hydroxy-acetophenone-directed Rh(III) catalyzed C-H o-alkylation via 1,4 addition: Insights from DFT and docking methodology
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Ganesh, Pothapragada S. K. Prabhakar
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JOURNAL OF MOLECULAR STRUCTURE, 2025, 1327
[32] Palladium-Catalyzed Annulation of Allenes with Indole-2-carboxylic Acid Derivatives: Synthesis of Indolo[2,3-c]pyrane-1-ones via Ar-I Reactivity or C-H Functionalization
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Swamy, K. C. Kumara
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (16): : 6959 - 6969
[33] Removal of the Pyridine Directing Group from α-Substituted N-(Pyridin-2-yl)piperidines Obtained via Directed Ru-Catalyzed sp3 C-H Functionalization
Smout, Veerle
Peschiulli, Aldo
Verbeeck, Stefan
Mitchell, Emily A.
Herrebout, Wouter
Bultinck, Patrick
Vande Velde, Christophe M. L.
Berthelot, Didier
Meerpoel, Lieven
Maes, Bert U. W.
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (19): : 9803 - 9814
[34] Synthesis of 7,7′-Dihydroxy-8,8′-biquinolyl (azaBINOL) via Pd-Catalyzed Directed Double C-H Functionalization of 8,8′-Biquinolyl: Emergence of an Atropos from a Tropos State
Wang, Chao
Flanigan, Darrin M.
Zakharov, Lev N.
Blakemore, Paul R.
ORGANIC LETTERS, 2011, 13 (15) : 4024 - 4027
[35] RETRACTION: Palladium-Catalyzed Decarboxylative Selective Acylation of 4H-Benzo[d] [1,3]oxazin-4-one Derivatives with α-Oxo Carboxylic Acids via Preferential Cyclic Imine-N-Directed Aryl C-H Activation (Retraction of Vol 358, Pg 283, 2016)
Majhi, Biju
Kundu, Debasish
Ghosh, Tubai
Ranua, Brindaban C.
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (03) : 700 - +
[36] RETRACTED: Palladium-Catalyzed Decarboxylative Selective Acylation of 4H-Benzo[d][1,3] oxazin-4-one Derivatives with α-Oxo Carboxylic acids via Preferential Cyclic Imine-N-Directed Aryl C-H Activation (Retracted article. See vol. 362, pg. 700, 2020)
Majhi, Biju
Kundu, Debasish
Ghosh, Tubai
Ranu, Brindaban C.
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (02) : 283 - 295

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