Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones To Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

被引：91

作者：

Gong, Liang ^{[1
,2
,3
]}

Sun, Hong-Bao ^{[1
,2
,3
]}

Deng, Li-Fan ^{[1
,2
,3
]}

Zhang, Xia ^{[1
,2
,3
]}

Liu, Jie ^{[1
,2
,3
]}

Yang, Shengyong ^{[1
,2
,3
]}

Niu, Dawen ^{[1
,2
,3
]}

机构：

[1] Sichuan Univ, West China Hosp, State Key Lab Biotherapy, Dept Emergency, Chengdu 610041, Sichuan, Peoples R China

[2] Sichuan Univ, West China Hosp, Ctr Canc, Chengdu 610041, Sichuan, Peoples R China

[3] Sichuan Univ, Sch Chem Engn, Chengdu 610041, Sichuan, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 19期

关键词：

BORONIC ACIDS; ARYLBORONIC ACIDS; BOND-CLEAVAGE; STEREOSELECTIVE-SYNTHESIS; TRANSITION-METALS; GRIGNARD-REAGENTS; CARBON-SULFUR; ACTIVATION; ELECTROPHILES; SULFONES;

D O I：

10.1021/jacs.9b02312

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We demonstrate that readily available and bench-stable alpha-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the alpha-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an alpha-heteroatom in facilitating these transformations.

引用

页码：7680 / 7686

页数：7

共 88 条

[1] Preparation of Quaternary Centers via Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Tertiary Sulfones [J].

Ariki, Zachary T. ;

Maekawa, Yuuki ;

Nambo, Masakazu ;

Crudden, Cathleen M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (01) :78-81

[2] Oxidative Heck Reaction of Glycals and Aryl Hydrazines: A Palladium-Catalyzed C-Glycosylation [J].

Bai, Yaguang ;

Kim, Le Mai Hoang ;

Liao, Hongze ;

Liu, Xue-Wei .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (17) :8821-8825

[3] Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation [J].

Basch, Corey H. ;

Liao, Jennie ;

Xu, Jianyu ;

Piane, Jacob J. ;

Watson, Mary P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (15) :5313-5316

[4] The first Suzuki cross-couplings of aryltrimethylammonium salts [J].

Blakey, SB ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) :6046-6047

[5] Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone? [J].

Brow, Dean G. ;

Bostrom, Jonas .

JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (10) :4443-4458

[6] N-Vinylpyridinium and -ammonium tetrafluoroborate salts:: New electrophilic coupling partners for Pd(0)-catalyzed Suzuki cross-coupling reactions [J].

Buszek, Keith R. ;

Brown, Neil .

ORGANIC LETTERS, 2007, 9 (04) :707-710

[7] NICKEL-CATALYZED SUBSTITUTIONS OF ARYL TERT-BUTYL SULFONES WITH ORGANOMETALLIC REAGENTS - SYNTHESIS OF ORTHO-SUBSTITUTED UNSYMMETRICAL BIARYLS [J].

CLAYDEN, J ;

COONEY, JJA ;

JULIA, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (01) :7-14

[8] ORTHO-SUBSTITUTED UNSYMMETRICAL BIARYLS FROM ARYL TERT-BUTYL SULFONES [J].

CLAYDEN, J ;

JULIA, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (22) :1682-1683

[9] Metal-catalyzed activation of ethers via C-O bond cleavage: a new strategy for molecular diversity [J].

Cornella, Josep ;

Zarate, Cayetana ;

Martin, Ruben .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (23) :8081-8097

[10] Breaking Amides using Nickel Catalysis [J].

Dander, Jacob E. ;

Garg, Neil K. .

ACS CATALYSIS, 2017, 7 (02) :1413-1423

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