Copper-catalyzed oxidative decarboxylative coupling of α-keto acids and sulfoximines

被引：40

作者：

Pimpasri, Chaleena ^{[1
]}

Sumunnee, Ladawan ^{[1
]}

Yotphan, Sirilata ^{[1
]}

机构：

[1] Mahidol Univ, Ctr Excellence Innovat Chem PERCH CIC, Dept Chem, Fac Sci, Bangkok 10400, Thailand

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 20期

关键词：

C-H ACTIVATION; HETEROAROMATIC CARBOXYLIC-ACIDS; OXOCARBOXYLIC ACIDS; ORTHO-ACYLATION; NH-SULFOXIMINES; ARYL BROMIDES; PALLADIUM; PHOTOREDOX; ARYLATION; AROYLATION;

D O I：

10.1039/c7ob00776k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed oxidative decarboxylative coupling of alpha-keto acids with NH-sulfoximines has been developed. With CuBr as the catalyst and K2S2O8 as the oxidant, this reaction enables the formation of a C-N bond and gives N-aroylsulfoximine products in moderate to excellent yields. The reaction mechanism is likely to involve the generation of a reactive aroyl radical intermediate.

引用

页码：4320 / 4327

页数：8

共 50 条

[21] Understanding copper-catalyzed oxidative decarboxylative coupling reactions through the reactivity of copper benzoate and copper aryl complexes
Bustin, Katelyn
Aguilera, Ellen
Burlas, Corrie
Hoover, Jessica
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[22] Intermediacy of Copper(I) under Oxidative Conditions in the Aerobic Copper-Catalyzed Decarboxylative Thiolation of Benzoic Acids
Green, Kerry-Ann
Hoover, Jessica M.
ACS CATALYSIS, 2020, 10 (03) : 1769 - 1782
[23] Copper-Catalyzed Decarboxylative Disulfonylation of Alkynyl Carboxylic Acids with Sulfinic Acids
Fu, Hong
Shang, Jia-Q
Yang, Tao
Shen, Yuehai
Gao, Chuan-Zhu
Li, Ya-Min
ORGANIC LETTERS, 2018, 20 (02) : 489 - 492
[24] Copper-Catalyzed Decarboxylative Difluoromethylation
Zeng, Xiaojun
Yan, Wenhao
Zacate, Samson B.
Chao, Tzu-Hsuan
Sun, Xiaodong
Cao, Zhi
Bradford, Kate G. E.
Paeth, Matthew
Tyndall, Sam B.
Yang, Kundi
Kuo, Tung-Chun
Cheng, Mu-Jeng
Liu, Wei
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (29) : 11398 - 11403
[25] Copper-catalyzed decarboxylative coupling reactions for the synthesis of proparal amines
Lim, Jeongah
Park, Kyungho
Byeun, Aleum
Lee, Sunwoo
TETRAHEDRON LETTERS, 2014, 55 (35) : 4875 - 4878
[26] Synthesis of Terminal Allenes via a Copper-Catalyzed Decarboxylative Coupling Reaction of Alkynyl Carboxylic Acids
Lim, Jeongah
Choi, Jinseop
Kim, Han-Sung
Kim, In Seon
Nam, Kye Chun
Kim, Jimin
Lee, Sunwoo
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (01): : 303 - 308
[27] Copper-Catalyzed Aerobic Oxidative/Decarboxylative Phosphorylation of Aryl Acrylic Acids with P(III)-Nucleophiles
Xiong, Biquan
Si, Lulu
Zhu, Longzhi
Liu, Yu
Xu, Weifeng
Tang, Ke-Wen
Yin, Shuang-Feng
Qian, Peng-Cheng
Wong, Wai-Yeung
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (17): : 12502 - 12518
[28] Copper-Catalyzed Decarboxylative Coupling of Alkenyl Acids with P(O)H Compounds at Room Temperature
Qiao, Huijie
Sun, Suyan
Kang, Jianxun
Yang, Fan
Wu, Yusheng
Wu, Yangjie
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (01) : 86 - 94
[29] Copper-Catalyzed Decarboxylative Cross- Coupling of α-Fluoroacrylic Acids with N-Tosyl Oxaziridines
Lu Xiaoyu
Sun Xiaomei
Niu Yaqing
Wang Junchao
Yin Wenjing
Gao Mengting
Liu Zi
Wei Zhenghuan
Tao Tinghua
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (06) : 2110 - 2119
[30] The Copper-Catalyzed Decarboxylative Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids
Bi, Hai-Peng
Zhao, Liang
Liang, Yong-Min
Li, Chao-Jun
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) : 792 - 795

← 1 2 3 4 5 →