Addition and coupling reactions of bis(pinacolato)diboron mediated by CuCl in the presence of potassium acetate

被引:237
作者
Takahashi, K [1 ]
Ishiyama, T [1 ]
Miyaura, N [1 ]
机构
[1] Hokkaido Univ, Grad Sch Engn, Div Mol Chem, Sapporo, Hokkaido 0608628, Japan
关键词
D O I
10.1246/cl.2000.982
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The addition of bis(pinacolato)diboron [(Me4C2O2)B-B(O2C2Me4)] to alpha,beta-unsaturated ketones, esters, nitriles, or terminal alkynes and the coupling with allyl chlorides were carried out in DMF at room temperature in the presence of CuCl and AcOK. The transmetalation from boron to copper generating a B-Cu species was proposed as the key step of the reactions.
引用
收藏
页码:982 / 983
页数:2
相关论文
共 20 条
[1]  
[Anonymous], 1994, ORGANOMETALLICS SYNT
[2]   THE SILYLCUPRATION OF ACETYLENES - A SYNTHESIS OF VINYLSILANES [J].
FLEMING, I ;
NEWTON, TW ;
ROESSLER, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09) :2527-2532
[3]   Synthesis of organoboron compounds via the transition metal-catalyzed addition and coupling reaction of (alkoxo)diborons [J].
Ishiyama, T ;
Miyaura, H .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1999, 57 (06) :503-511
[4]   Platinum(0)-catalyzed diboration of alkynes with tetrakis(alkoxo)diborons: An efficient and convenient approach to cis-bis(boryl) alkenes [J].
Ishiyama, T ;
Matsuda, N ;
Murata, M ;
Ozawa, F ;
Suzuki, A ;
Miyaura, N .
ORGANOMETALLICS, 1996, 15 (02) :713-720
[5]   Diboration of alkenes with bis(pinacolato)diboron catalysed by a platinum(0) complex [J].
Ishiyama, T ;
Yamamoto, M ;
Miyaura, N .
CHEMICAL COMMUNICATIONS, 1997, (07) :689-690
[6]   Platinum(0)-catalysed diboration of alka-1,3-dienes with bis(pinacolato)diboron [J].
Ishiyama, T ;
Yamamoto, M ;
Miyaura, N .
CHEMICAL COMMUNICATIONS, 1996, (17) :2073-2074
[7]   PLATINUM(O)-CATALYZED DIBORATION OF ALKYNES [J].
ISHIYAMA, T ;
MATSUDA, N ;
MIYAURA, N ;
SUZUKI, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :11018-11019
[8]  
ISHIYAMA T, UNPUB
[9]  
ITO H, 2000, IN PRESS TETRAHEDRON
[10]   Mechanistic investigation of stoichiometric alkyne insertion into Pt-B bonds and related chemistry bearing on the catalytic diborylation of alkynes mediated by platinum(II) diboryl complexes [J].
Iverson, CN ;
Smith, MR .
ORGANOMETALLICS, 1996, 15 (24) :5155-5165