Synthesis of Aryl Trimethylstannanes from Aryl Amines: A Sandmeyer-Type Stannylation Reaction

被引:83
作者
Qiu, Di [1 ,2 ]
Meng, He [1 ,2 ]
Jin, Liang [1 ,2 ]
Wang, Shuai [1 ,2 ]
Tang, Shengbo [1 ,2 ]
Wang, Xi [1 ,2 ]
Mo, Fanyang [1 ,2 ]
Zhang, Yan [1 ,2 ]
Wang, Jianbo [1 ,2 ,3 ]
机构
[1] Peking Univ, Coll Chem, Minist Educ, Beijing Natl Lab Mol Sci BNLMS, Beijing 100871, Peoples R China
[2] Peking Univ, Coll Chem, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
关键词
aryl stannanes; cross-coupling; diazonium salts; Sandmeyer reaction; Stille coupling reaction; CROSS-COUPLING REACTIONS; METAL-FREE BORYLATION; ORGANIC HALIDES; ORGANOTIN COMPOUNDS; DIRECT CONVERSION; RADICAL-ADDITION; DIAZONIUM SALTS; ALKYL NITRITES; PALLADIUM; ARYLAMINES;
D O I
10.1002/anie.201304579
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Sandmeyer-type stannylation: Stille coupling is one of the most powerful coupling reactions for C-C bond formation, whereas there are only limited methods to access aryl stannane compounds. A mild stannylation process based on a Sandmeyer-type transformation using aromatic amines as the starting materials is described. DCE: 1,2-dichloroethane. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:11581 / 11584
页数:4
相关论文
共 58 条
[51]   GENERATION OF FLUOROCHLOROCARBENE BY MERCURIAL ROUTE [J].
SEYFERTH, D ;
DARRAGH, KV .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1968, 11 (01) :P9-&
[52]   Two-step synthesis of di- and tristannylarenes from anilines via an SRN1 mechanism [J].
Silbestri, Gustavo F. ;
Lockhart, Maria T. ;
Chopa, Alicia B. .
ARKIVOC, 2011, :210-220
[53]   SYNTHETIC METHODS .15. UNSATURATED ACYL DERIVATIVES OF SILICON, GERMANIUM, AND TIN FROM METALATED ENOL ETHERS [J].
SODERQUIST, JA ;
HASSNER, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (05) :1577-1583
[54]   THE PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOTIN REAGENTS WITH ORGANIC ELECTROPHILES [J].
STILLE, JK .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (06) :508-523
[55]   Silver-Catalyzed Late-Stage Fluorination [J].
Tang, Pingping ;
Furuya, Takeru ;
Ritter, Tobias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (34) :12150-12154
[56]   Evolution and Synthetic Applications of the Heck-Matsuda Reaction: The Return of Arenediazonium Salts to Prominence [J].
Taylor, Jason G. ;
Moro, Angelica Venturini ;
Correia, Carlos Roque D. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (08) :1403-1428
[57]   A REGIOSELECTIVE ENTRY TO VINYLLITHIUMS FROM UNSYMMETRICAL KETONES VIA ENOL TRIFLATES [J].
WULFF, WD ;
PETERSON, GA ;
BAUTA, WE ;
CHAN, KS ;
FARON, KL ;
GILBERTSON, SR ;
KAESLER, RW ;
YANG, DC ;
MURRAY, CK .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (02) :277-279
[58]   Transition-Metal-Free Borylation of Aryltriazene Mediated by BF3•OEt2 [J].
Zhu, Chuan ;
Yamane, Motoki .
ORGANIC LETTERS, 2012, 14 (17) :4560-4563