Direct Access to Chiral Secondary Amides by Copper-Catalyzed Borylative Carboxamidation of Vinylarenes with Isocyanates

被引：68

作者：

Fiorito, Daniele ^{[1
]}

Liu, Yangbin ^{[1
]}

Besnard, Celine ^{[2
]}

Mazet, Clement ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, 30 Quai Ernest Ansermet, CH-1211 Geneva, Switzerland

[2] Univ Geneva, Lab Crystallog, 24 Quai Ernest Ansermet, CH-1211 Geneva, Switzerland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2020年 / 142卷 / 01期

基金：

瑞士国家科学基金会;

关键词：

ASYMMETRIC HYDROBORATION; IN-SITU; CYCLOADDITION; AMIDATION; LIGANDS; ALKENES; AMINOBORATION; ARYLBORATION; CYCLIZATION; 1,3-DIENES;

D O I：

10.1021/jacs.9b12297

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Cu-catalyzed borylative carboxamidation reaction has been developed using vinylarenes and isocyanates. Alkynes, branched 1,3-dienes, and bicyclic alkenes were also found to be competent coupling partners. Using a chiral phosphanamine ligand, an enantioselective variant of this transformation was developed, affording a set of alpha-chiral amides with unprecedented levels of enantioselectivity. The synthetic utility of the method was demonstrated through a series of representative stereoretentive postcatalytic derivatizations.

引用

页码：623 / 632

页数：10

共 50 条

[41] Copper-Catalyzed Dehydration of Primary Amides to Nitriles
Stephan Enthaler
Maik Weidauer
Catalysis Letters, 2011, 141
[42] Copper-Catalyzed Regioselective ortho C-H Cyanation of Vinylarenes
Yang, Yang
Buchwald, Stephen L.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (33) : 8677 - 8681
[43] Copper-Catalyzed Direct Transformation of Secondary Allylic and Benzylic Alcohols into Azides and Amides: An Efficient Utility of Azide as a Nitrogen Source
Rokade, Balaji V.
Gadde, Karthik
Prabhu, Kandikere Ramaiah
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (12) : 2706 - 2717
[44] Ligand-free copper-catalyzed borylative defluorination: access to gem-difluoroallyl boronic acid derivatives
Gates, Ashley M.
Jos, Swetha
Santos, Webster L.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (02) : 366 - 374
[45] Ligand-free copper-catalyzed borylative defluorination: access to gem-difluoroallyl boronic acid derivatives
Gates, Ashley M.
Jos, Swetha
Santos, Webster L.
Organic and Biomolecular Chemistry, 2022, 20 (02): : 366 - 374
[46] Enantioselective Copper-Catalyzed Alkylation of Quinoline N-Oxides with Vinylarenes
Yu, Songjie
Sang, Hui Leng
Ge, Shaozhong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (50) : 15896 - 15900
[47] Photoinduced, Copper-Catalyzed Alkylation of Amides with Unactivated Secondary Alkyl Halides at Room Temperature
Hien-Quang Do
Bachman, Shoshana
Bissember, Alex C.
Peters, Jonas C.
Fu, Gregory C.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (05) : 2162 - 2167
[48] Enantioselective Copper-Catalyzed Intermolecular Cyanobenzoyldifluoromethylation of Alkenes: Access to Chiral β-Difluoroacyl Nitriles
Fang, Mougui
Wu, Pingjie
Wang, Xia
Xie, Ziyue
Hou, Yali
Liu, Yao
Wu, Jingjing
Wu, Fanhong
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (06): : 4107 - 4111
[49] Selective Formation of Secondary Amides via the Copper-Catalyzed Cross-Coupling of Alkylboronic Acids with Primary Amides
Rossi, Steven A.
Shimkin, Kirk W.
Xu, Qun
Mori-Quiroz, Luis M.
Watson, Donald A.
ORGANIC LETTERS, 2013, 15 (09) : 2314 - 2317
[50] Copper-catalyzed aerobic oxidative cross-coupling reactions of vinylarenes with sulfinate salts: A direct approach to β-ketosulfones
Chen, Yu
Xu, Lei
Wang, Biyu
Jiang, Jingjing
Sun, Yixiang
Li, Longchun
TETRAHEDRON LETTERS, 2021, 65

← 1 2 3 4 5 →