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
[1]   Design and Synthesis of Skeletal Analogues of Gambierol: Attenuation of Amyloid-β and Tau Pathology with Voltage-Gated Potassium Channel and N-Methyl-D-aspartate Receptor Implications [J].
Alonso, Eva ;
Fuwa, Haruhiko ;
Vale, Carmen ;
Suga, Yuto ;
Goto, Tomomi ;
Konno, Yu ;
Sasaki, Makoto ;
LaFerla, Frank M. ;
Vieytes, Mercedes R. ;
Gimenez-Llort, Lydia ;
Botana, Luis M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (17) :7467-7479
[2]  
[Anonymous], 2012, ANGEW CHEM, V124, P5150
[3]  
[Anonymous], 1986, Angew. Chem
[4]   REACTIONS OF ORGANIC HALIDES WITH R3MMR3 COMPOUNDS (M=SI,GE,SN) IN PRESENCE OF TETRAKIS(TRIARYLPHOSPHINE) PALLADIUM [J].
AZARIAN, D ;
DUA, SS ;
EABORN, C ;
WALTON, DRM .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 117 (03) :C55-C57
[5]   SYNTHESIS OF ORGANOTRIALKYLSTANNANES - THE REACTION BETWEEN ORGANIC HALIDES AND HEXAALKYLDISTANNANES IN THE PRESENCE OF PALLADIUM COMPLEXES [J].
AZIZIAN, H ;
EABORN, C ;
PIDCOCK, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 215 (01) :49-58
[6]   On aromatic fluoric compounds, I A new method for its representation [J].
Balz, G ;
Schiemann, G .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1927, 60 :1186-1190
[8]  
Bohlmann R., 1991, COMPREHENSIVE ORGANI, V6, P203
[9]  
BUMAGIN NA, 1984, DOKL AKAD NAUK SSSR+, V274, P1103
[10]   Synthesis of arylstannanes from arylamines [J].
Chopa, AB ;
Lockhart, MT ;
Silbestri, G .
ORGANOMETALLICS, 2001, 20 (15) :3358-3360