Directing Group in Decarboxylative Cross-Coupling: CopperCatalyzed Site-Selective C-N Bond Formation from Nonactivated Aliphatic Carboxylic Acids

被引：68

作者：

Liu, Zhao-Jing ^{[1
]}

Lu, Xi ^{[1
]}

Wang, Guan ^{[1
]}

Li, Lei ^{[1
]}

Jiang, Wei-Tao ^{[1
]}

Wang, Yu-Dong ^{[1
]}

Xiao, Bin ^{[1
]}

Fu, Yao ^{[1
]}

机构：

[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, CAS Key Lab Urban Pollutant Convers, Anhui Prov Key Lab Biomass Clean Energy,IChEM, Anhua 230026, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 30期

关键词：

ELECTRON TRANSFER; ALKYL-HALIDES; PALLADIUM; FUNCTIONALIZATION; DIAMINATION; PHOTOREDOX; HETEROCYCLES; OXIDATION; AMINATION; MECHANISM;

D O I：

10.1021/jacs.6b05788

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Copper-catalyzed directed decarboxylative amination of nonactivated aliphatic carboxylic acids is described. This intramolecular C-N bond formation reaction provides efficient access to the synthesis of pyrrolidine and piperidine derivatives as well as the modification of complex natural products. Moreover, this reaction presents excellent site selectivity in the C-N bond formation step through the use of directing group. Our work can be considered as a big step toward controllable radical decarboxylative carbon-heteroatom cross-coupling.

引用

页码：9714 / 9719

页数：6

共 47 条

[31] PhI(OAc)2/I2-Mediated Decarboxylative C4-Amination of Coumarin-3-Carboxylic Acids via Csp2-H Dehydrogenative C-N Cross-Coupling under Ambient Conditions
Bhowmick, Anindita
Brahmachari, Goutam
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023,
[32] Iodine-Promoted Oxidative Cross-Coupling of Unprotected Anilines with Methyl Ketones: A Site-Selective Direct C-H Bond Functionalization to C4-Dicarbonylation of Anilines
Wu, Xia
Gao, Qinghe
Geng, Xiao
Zhang, Jingjing
Wu, Yan-dong
Wu, An-xin
ORGANIC LETTERS, 2016, 18 (10) : 2507 - 2510
[33] C(sp)-C(sp3) Bond Formation through Ligand- and Additive-Free CuO-Mediated Decarboxylative Direct Cross-Coupling of Coumarin-/Chromone-3-carboxylic Acids and Terminal Alkynes
Bhowmick, Anindita
Brahmachari, Goutam
ORGANIC LETTERS, 2023, 25 (39) : 7095 - 7099
[34] Catalyst-free electrochemical decarboxylative cross-coupling of N-hydroxyphthalimide esters and N-heteroarenes towards C(sp3)-C(sp2) bond formation
Liu, Yichang
Xue, Liwei
Shi, Biyin
Bu, Faxiang
Wang, Dan
Lu, Lijun
Shi, Renyi
Lei, Aiwen
CHEMICAL COMMUNICATIONS, 2019, 55 (99) : 14922 - 14925
[35] The first phosphine oxide ligand precursors for transition metal catalyzed cross-coupling reactions: C-C, C-N, and C-S bond formation on unactivated aryl chlorides
Li, GY
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (08) : 1513 - +
[36] The first phosphine oxide ligand precursors for transition metal catalyzed cross-coupling reactions: C-C, C-N, and C-S bond formation on unactivated aryl chlorides
Li, G.Y. (george.y.li@usa.dupont.com), 2001, Wiley-VCH Verlag (40)
[37] Nickel-Catalyzed Diaryl Ketone Synthesis by N-C Cleavage: Direct Negishi Cross-Coupling of Primary Amides by Site-Selective N,N-Di-Boc Activation
Shi, Shicheng
Szostak, Michal
ORGANIC LETTERS, 2016, 18 (22) : 5872 - 5875
[38] Copper-catalyzed C-N bond cross-coupling of aryl halides and amines in water in the presence of ligand derived from oxalyl dihydrazide: scope and limitation
Kurandina, D. V.
Eliseenkov, E. V.
Khaibulova, T. S.
Petrov, A. A.
Boyarskiy, V. P.
TETRAHEDRON, 2015, 71 (41) : 7931 - 7937
[39] Fabrication, characterization and application of nanopolymer supported copper (II) complex as an effective and reusable catalyst for the C-N bond cross-coupling reaction of sulfonamides with arylboronic acids in water under aerobic conditions
Nasrollahzadeh, Mahmoud
Rostami-Vartooni, Akbar
Ehsani, Ali
Moghadam, Majid
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 387 : 123 - 129
[40] An efficient synthesis of N-substituted indoles from indoline/indoline carboxylic acid via aromatization followed by C-N cross-coupling reaction by using nano copper oxide as a recyclable catalyst
Reddy, K. Harsha Vardhan
Satish, G.
Ramesh, K.
Karnakar, K.
Nageswar, Y. V. D.
TETRAHEDRON LETTERS, 2012, 53 (24) : 3061 - 3065

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