Palladium-Catalyzed ipso-Borylation of Aryl Sulfides with Diborons

被引：53

作者：

Bhanuchandra, M. ^{[1
]}

Baralle, Alexandre ^{[1
]}

Otsuka, Shinya ^{[1
]}

Nogi, Keisuke ^{[1
]}

Yorimitsu, Hideki ^{[1
]}

Osuka, Atsuhiro ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 12期

关键词：

CROSS-COUPLING REACTION; C-S ACTIVATION; BORONIC ACIDS; BOND FORMATION; METAL; CHLORIDES; SULFUR; FLUOROARENES; REACTIVITY; LITHIATION;

D O I：

10.1021/acs.orglett.6b01305

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic Miyaura-type ipso-borylation of aryl sulfides with diboron reagents has been achieved, providing arylboronate esters of synthetic use. The key conditions to transform inherently reluctant C-S bonds into C-B bonds include a palladium-NHC (N-heterocyclic carbene) Precatalyst, bis(pinacolato)diboron, and lithium hexamethyldisilazide. This protocol is applicable to a reasonable range of aryl alkyl sulfides. Twofold borylation was observed in the reaction of diphenyl sulfide.

引用

页码：2966 / 2969

页数：4

共 70 条

[1] Unusual influence of the structures of transition metal complexes on catalytic C-S and C-Se bond formation under homogeneous and heterogeneous conditions [J].

Beletskaya, Irina P. ;

Ananikov, Valentine P. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (21) :3431-3444

[2] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].

Beletskaya, Irina P. ;

Ananikov, Valentine P. .

CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636

[3] Palladium-catalyzed borylation of aryl chlorides: Scope, applications, and computational studies [J].

Billingsley, Kelvin L. ;

Barder, Timothy E. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (28) :5359-5363

[4]

Block E., 1994, Advances in Sulfur Chemistry

[5] A decade advancement of transition metal-catalyzed borylation of aryl halides and sulfonates [J].

Chow, Wing Kin ;

Yuen, On Ying ;

Choy, Pui Ying ;

So, Chau Ming ;

Lau, Chak Po ;

Wong, Wing Tak ;

Kwong, Fuk Yee .

RSC ADVANCES, 2013, 3 (31) :12518-12539

[6] Carbon-Boron Bond Cross-Coupling Reaction Catalyzed by -PPh2 Containing Palladium-Indolylphosphine Complexes [J].

Chow, Wing Kin ;

Yuen, On Ying ;

So, Chau Ming ;

Wong, Wing Tak ;

Kwong, Fuk Yee .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (07) :3543-3548

[7] Synthesis of nitrodienes, nitrostyrenes, and nitrobiaryls through palladium-catalyzed couplings of β-nitrovinyl and o-nitroaryl thioethers [J].

Creech, Gardner S. ;

Kwon, Ohyun .

CHEMICAL SCIENCE, 2013, 4 (06) :2670-2674

[8]

Cremlyn RJW., 1996, INTRO ORGANOSULFUR C

[9] Near Room Temperature Cross-Coupling Reactions of Arene Boronic Acids with a Quinoxaline 1,4-Dioxide Benzylsulfanyl Derivative [J].

Dahbi, Samir ;

Bisseret, Philippe .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (20) :3759-3763

[10] Organosulfur compounds: Electrophilic reagents in transition-metal-catalyzed carbon-carbon bond-forming reactions [J].

Dubbaka, SR ;

Vogel, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (47) :7674-7684

← 1 2 3 4 5 6 7 →