Chemo- and Enantioselective Arylation and Alkenylation of Aldehydes Enabled by Nickel/N-Heterocyclic Carbene Catalysis

被引：31

作者：

Wang, Zi-Chao ^{[1
]}

Gao, Jian ^{[1
]}

Cai, Yuan ^{[1
]}

Ye, Xiaodong ^{[1
]}

Shi, Shi-Liang ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem,Ctr Excellence Mo, Shanghai 200032, Peoples R China

[2] Fudan Univ, Sch Pharm, Shanghai 201203, Peoples R China

来源：

CCS CHEMISTRY | 2022年 / 4卷 / 04期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; nickel; arylation; alkenylation; chiral NHC ligand; chemoselectivity; chiral secondary alcohol; ARYLBORONIC ACIDS; INTRAMOLECULAR ADDITION; ASYMMETRIC ARYLATION; ORGANOBORONIC ACIDS; BORONIC ACIDS; ARYL; KETONES; ALCOHOLS; ESTERS; ETA(2)-ALDEHYDE;

D O I：

10.31635/ccschem.021.202101001

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report the first highly enantioselective Ni-catalyzed arylation and alkenylation of simple aldehydes using readily available and stable organoboronic esters. This protocol provides various chiral secondary alcohols in high yields and enantioselectivities (up to 97% ee) with a broad scope of substrates, functional groups, and heterocycles. The use of a bulky N-heterocyclic carbene (NHC) ligand for nickel catalyst is the key to high enantiocontrol. The competitive Ni-catalyzed transformations, including Tishchenko reaction, dehydrogenation/hydrogenation reaction, and Suzuki-Miyaura couplings, are avoided. The excellent chemoselectivity is likely due to the application of mild base CsF and eta(2)-coordination of aldehydes with nickel. [GRAPHICS] .

引用

页码：1169 / 1179

页数：11

共 69 条

[1]

[Anonymous], 2019, J Am Chem Soc, P141

[2]

[Anonymous], 2023, COMPREHENSIVE ORGANO, DOI DOI 10.1016/J.FISHRES.2023.106825

[3]

BAROUH V, 1971, J MED CHEM, V14, P834

[4] Ni-catalysed, domino synthesis of tertiary alcohols from secondary alcohols [J].

Berini, Christophe ;

Navarro, Oscar .

CHEMICAL COMMUNICATIONS, 2012, 48 (10) :1538-1540

[5] Rapid and Selective Catalytic Oxidation of Secondary Alcohols at Room Temperature by Using (N-Heterocyclic Carbene)-Ni0 Systems [J].

Berini, Christophe ;

Winkelmann, Ole H. ;

Otten, Jennifer ;

Vicic, David A. ;

Navarro, Oscar .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (23) :6857-6860

[6] Catalyzed asymmetric aryl transfer reactions to aldehydes with boronic acids as aryl source [J].

Bolm, C ;

Rudolph, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) :14850-14851

[7] Nucleophilic displacement at benzhydryl centers: Asymmetric synthesis of 1,1-diarylalkyl derivatives [J].

Bolshan, Y ;

Chen, CY ;

Chilenski, JR ;

Gosselin, F ;

Mathre, DJ ;

O'Shea, PD ;

Roy, A ;

Tillyer, RD .

ORGANIC LETTERS, 2004, 6 (01) :111-114

[8] A Nickel Catalyst for the Addition of Organoboronate Esters to Ketones and Aldehydes [J].

Bouffard, Jean ;

Itami, Kenichiro .

ORGANIC LETTERS, 2009, 11 (19) :4410-4413

[9] Chiral Allene-Containing Phosphines in Asymmetric Catalysis [J].

Cai, Feng ;

Pu, Xiaotao ;

Qi, Xiangbing ;

Lynch, Vincent ;

Radha, Akella ;

Ready, Joseph M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (45) :18066-18069

[10] Fast Enantio- and Chemoselective Arylation of Ketones with Organoboronic Esters Enabled by Nickel/N-Heterocyclic Carbene Catalysis [J].

Cai, Yuan ;

Ruan, Lin-Xin ;

Rahman, Abdul ;

Shi, Shi-Liang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (10) :5262-5267

← 1 2 3 4 5 6 7 →