Nickel-Catalyzed Cross Couplings of Benzylic Ammonium Salts and Boronic Acids: Stereospecific Formation of Diarylethanes via C-N Bond Activation

被引：252

作者：

Maity, Prantik ^{[1
]}

Shacklady-McAtee, Danielle M. ^{[1
]}

Yap, Glenn P. A. ^{[1
]}

Sirianni, Eric R. ^{[1
]}

Watson, Mary P. ^{[1
]}

机构：

[1] Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 01期

基金：

美国国家科学基金会;

关键词：

ASYMMETRIC-SYNTHESIS; ARYLTRIMETHYLAMMONIUM IODIDES; ARYLBORONIC ACIDS; NEGISHI REACTIONS; CARBONATES; ALKYLATION; REAGENTS; PROTODEBORONATION; TRIARYLMETHANES; DIARYLMETHANES;

D O I：

10.1021/ja3089422

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have developed a nickel-catalyzed cross coupling of benzylic ammonium triflates with aryl boronic acids to afford diarylmethanes and diarylethanes. This reaction proceeds under mild reaction conditions and with exceptional functional group tolerance. Further, it transforms branched benzylic ammonium salts to diarylethanes with excellent chirality transfer, offering a new strategy for the synthesis of highly enantioenriched diarylethanes from readily available chiral benzylic amines.

引用

页码：280 / 285

页数：6

共 50 条

[41] Nickel-catalyzed Heck cross couplings via activation of strong C-O bonds
Ehle, Andrew R.
Zhou, Qi
Watson, Mary P.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[42] Nickel-Catalyzed Cross-Coupling Reaction of Aryl Bromides/Nitriles with Imidazolium Salts Involving Inert C-N Bond Cleavage
Jin, Zhou
Yang, Yanhao
He, Zhichang
Huang, Zhengzhe
Hu, Yuanyuan
Jin, Hongwei
Zhou, Bingwei
ORGANIC LETTERS, 2024, 26 (21) : 4520 - 4525
[43] Progress on Transition-Metal-Catalyzed Cross-Coupling Reactions of Ammonium Salts via C-N Bond Cleavage
Li, Gang
Chen, Ye
Xia, Jibao
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (08) : 1949 - 1962
[44] Organozinc-Mediated Direct C-C Bond Formation via C-N Bond Cleavage of Ammonium Salts
Wang, Dong-Yu
Morimoto, Koki
Yang, Ze-Kun
Wang, Chao
Uchiyama, Masanobu
CHEMISTRY-AN ASIAN JOURNAL, 2017, 12 (19) : 2554 - 2557
[45] ORGN 484-Copper-catalyzed C-N bond formation: The cross-coupling of oxime esters and vinyl boronic acids
Liu, Songbai
Yu, Ying
Liebeskind, Lanny S.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
[46] Nickel-Catalyzed C-S Bond Formation: Synthesis of Aryl Sulfides from Arylsulfonyl Hydrazides and Boronic Acids
Singh, Rahul
Allam, Bharat Kumar
Singh, Neetu
Kumari, Kumkum
Singh, Satish Kumar
Singh, Krishna Nand
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (06) : 1181 - 1186
[47] Copper-Catalyzed Imino C-N Bond Formation with Aryl Boronic Acids under Aerobic Conditions
Mandal, Prashant S.
Kumar, A. Vijay
SYNLETT, 2016, 27 (09) : 1408 - 1412
[48] Mechanism of Nickel-Catalyzed Selective C-N Bond Activation in Suzuki-Miyaura Cross-Coupling of Amides: A Theoretical Investigation
Liu, Liu
Chen, Peng
Sung, Ying
Wu, Yile
Chen, Su
Zhu, Jun
Zhae, Yufen
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (23): : 11686 - 11696
[49] Stereospecific cross-coupling reactions via nickel-catalyzed ring opening reactions of benzylic ethers and lactones
Tollefson, Emily J.
Osborne, Charlotte A.
Dawson, David D.
Jarvo, Elizabeth R.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[50] Conversion of Amides into Esters by the Nickel-Catalyzed Activation of Amide C-N Bonds
Garg, Neil
Houk, Kendall N.
Baker, Emma L.
Nathel, Noah F. Fine
Hie, Liana
Hong, Xin
Liu, Peng
Shah, Tejas K.
Yang, Yun-fang
SYNLETT, 2016, 27 (01) : A3 - A8

← 1 2 3 4 5 →