Palladium-Catalyzed Cross-Coupling of Unactivated Aryl Sulfides with Arylzinc Reagents under Mild Conditions

被引：51

作者：

Otsuka, Shinya ^{[1
]}

Fujino, Daishi ^{[1
]}

Murakami, Kei ^{[1
,2
]}

Yorimitsu, Hideki ^{[1
,3
]}

Osuka, Atsuhiro ^{[1
]}

机构：

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

[2] Hakubi Ctr Adv Res, Sakyo Ku, Kyoto 6068502, Japan

[3] JST, ACT C, Sakyo Ku, Kyoto 6068502, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 41期

关键词：

cross-coupling; C-S bond activation; organosulfur compounds; organozic compounds; palladium; BOND-FORMING REACTIONS; C-S ACTIVATION; GRIGNARD-REAGENTS; CARBON-CARBON; ARYLBORONIC ACIDS; HETEROAROMATIC THIOETHER; PUMMERER REACTION; ORGANIC-SYNTHESIS; BORONIC ACIDS; THIOL ESTERS;

D O I：

10.1002/chem.201404380

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cross-coupling of general aryl alkyl sulfides with arylzinc reagents proceeds smoothly, even at room temperature or below, with a palladium N-heterocyclic carbene (NHC) catalyst. When combined with reactions that are unique to organosulfurs, that is, the SNAr sulfanylation or Pummerer reaction, the cross-coupling offers interesting transformations that are otherwise difficult to achieve. An alkylsulfanyl group is preferentially converted whilst leaving the tosyloxy and chloro intact, which expands the variety of orthogonal cross-coupling.

引用

页码：13146 / 13149

页数：4

共 141 条

[51] Bioinspired organometallic chemistry [J].

Liebeskind, LS ;

Srogl, J ;

Savarin, C ;

Polanco, C .

PURE AND APPLIED CHEMISTRY, 2002, 74 (01) :115-122

[52] Heteroaromatic thioether-boronic acid cross-coupling under neutral reaction conditions [J].

Liebeskind, LS ;

Srogl, J .

ORGANIC LETTERS, 2002, 4 (06) :979-981

[53] Thiol ester-boronic acid coupling. A mechanistically unprecedented and general ketone synthesis [J].

Liebeskind, LS ;

Srogl, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (45) :11260-11261

[54] Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions [J].

Littke, AF ;

Dai, CY ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4020-4028

[55]

Littke AF, 2002, ANGEW CHEM INT EDIT, V41, P4176, DOI 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO

[56]

2-U

[57]

Littke AF., 2002, Angew Chem, V114, P4350, DOI [10.1002/1521-3757(20021115)114:223.0.CO

[58]

2-0, DOI 10.1002/1521-3757(20021115)114:223.0.CO

[59]

2-0]

[60] Pd-Catalyzed C-S Activation for [3+3] Annulation of 2-(Methylthio)benzofuran-3-carboxylates and 2-Hydroxyphenylboronic Acids: Synthesis of Coumestan Derivatives [J].

Liu, Jingxin ;

Liu, Yingjie ;

Du, Wenting ;

Dung, Ying ;

Liu, Jun ;

Wang, Mang .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (14) :7293-7297

← 1 2 3 4 5 6 7 8 9 10 →