Direct Thioamination of Arynes via Reaction with Sulfilimines and Migratory N-Arylation

被引：119

作者：

Yoshida, Suguru ^{[1
]}

Yano, Takahisa ^{[1
]}

Misawa, Yoshihiro ^{[1
]}

Sugimura, Yasuyuki ^{[2
]}

Igawa, Kazunobu ^{[3
]}

Shimizu, Shigeomi ^{[2
]}

Tomooka, Katsuhiko ^{[3
]}

Hosoya, Takamitsu ^{[1
]}

机构：

[1] Tokyo Med & Dent Univ, Inst Biomat & Bioengn, Lab Chem Biosci, Chiyoda Ku, Tokyo 1010062, Japan

[2] Tokyo Med & Dent Univ, Med Res Inst, Dept Pathol Cell Biol, Bunkyo Ku, Tokyo 1138510, Japan

[3] Kyushu Univ, Inst Mat Chem & Engn, Kasuga, Fukuoka 8168580, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 44期

关键词：

BOND FORMATION; SYNTHETIC APPLICATIONS; NUCLEOPHILIC-ADDITION; EXCHANGE-REACTION; CONCISE SYNTHESIS; CARBON-CARBON; GENERATION; INSERTION; ACTIVATION; BENZYNE;

D O I：

10.1021/jacs.5b10557

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel method for preparing a diverse range of o-sulfanylanilines is described. Direct thioamination of arynes with sulfilimines gives o-sulfanylanilines, involving C-N and C-S bond formations and migratory N-arylation.

引用

页码：14071 / 14074

页数：4

共 62 条

[41] Diversity-oriented synthesis leads to an effective class of bifunctional linchpins uniting anion relay chemistry (ARC) with benzyne reactivity [J].

Smith, Amos B., III ;

Kim, Won-Suk .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2011, 108 (17) :6787-6792

[42] Boron-Selective Biaryl Coupling Approach to Versatile Dibenzoxaborins and Application to Concise Synthesis of Defucogilvocarcin M [J].

Sumida, Yuto ;

Harada, Ryu ;

Kato-Sumida, Tomoe ;

Johmoto, Kohei ;

Uekusa, Hidehiro ;

Hosoya, Takamitsu .

ORGANIC LETTERS, 2014, 16 (23) :6240-6243

[43] Generation of Arynes via Ate Complexes of Arylboronic Esters with an ortho-Leaving Group [J].

Sumida, Yuto ;

Kato, Tomoe ;

Hosoya, Takamitsu .

ORGANIC LETTERS, 2013, 15 (11) :2806-2809

[44] A Comprehensive History of Arynes in Natural Product Total Synthesis [J].

Tadross, Pamela M. ;

Stoltz, Brian M. .

CHEMICAL REVIEWS, 2012, 112 (06) :3550-3577

[45]

Takata T., 2014, CONT ORGANOSULFUR CH

[46]

Taylor PC., 1999, Sulfur Rep, V21, P241

[47] Development of a Concise Synthesis of (-)-Oseltamivir (Tamiflu) [J].

Trost, Barry M. ;

Zhang, Ting .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (13) :3630-3643

[48]

Whitham G.H., 1995, ORGANOSULFUR CHEM

[49]

Yoshida H, 2015, MULTICOMPONENT REACTIONS IN ORGANIC SYNTHESIS, P39

[50] Synchronous Ar-F and Ar-Sn Bond Formation through Fluorostannylation of Arynes [J].

Yoshida, Hiroto ;

Yoshida, Ryuma ;

Takaki, Ken .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (33) :8629-8632

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