Application of fluoride-catalyzed silane reductions of tin halides to the in situ preparation of vinylstannanes

被引:31
作者
Maleczka, RE [1 ]
Terrell, LR [1 ]
Clark, DH [1 ]
Whitehead, SL [1 ]
Gallagher, WP [1 ]
Terstiege, I [1 ]
机构
[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
关键词
D O I
10.1021/jo990491+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have found that either Bu3SnCl/PMHS/KF(aq), or the combination of tributyltin fluoride, PMHS, and catalytic quantities of tetrabutylammonium fluoride can serve as in situ sources of tributyltin hydride for both free radical and palladium-catalyzed hydrostannylation reactions. These methods are tolerant of a variety of functional groups, including silyl ethers, Furthermore, Me3SnCl is also reduced under these conditions, providing a relatively convenient and safe manner by which Me3SnH can be formed and reacted. We have also observed that the Bu3SnCl/siloxane/fluoride combination offers improvements over the existing protocols for transforming 1-bromoalkynes into trans-1-(tributylstannyl)-1-alkenes. Specifically, the KF/PMHS methodology allows the 1-bromoalkyne to be formed and reacted in a single pot and with substoichiometric amounts of tin. Finally, alternative reductants such as Red-Sil are also amenable to the method.
引用
收藏
页码:5958 / 5965
页数:8
相关论文
共 44 条
[1]  
Alcaraz L, 1997, SYNLETT, P791
[2]   Radical hydrostannylation, Pd(0)-catalyzed hydrostannylation, stannylcupration of propargyl alcohols and enynols: Regio- and stereoselectivities [J].
Betzer, JF ;
Delaloge, F ;
Muller, B ;
Pancrazi, A ;
Prunet, J .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7768-7780
[3]   Solid-phase preparation of dienes [J].
Blaskovich, MA ;
Kahn, M .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1119-1125
[4]   Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes [J].
Boden, CDJ ;
Pattenden, G ;
Ye, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (20) :2417-2419
[5]   HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].
BRESLOW, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164
[6]   1993 RU-LEMIEUX-AWARD-LECTURE - ORGANOMETALLIC-TYPE REACTIONS IN AQUEOUS-MEDIA - A NEW CHALLENGE IN ORGANIC-SYNTHESIS [J].
CHAN, TH ;
LI, CJ ;
LEE, MC ;
WEI, ZY .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (05) :1181-1192
[7]   REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES [J].
CHUIT, C ;
CORRIU, RJP ;
REYE, C ;
YOUNG, JC .
CHEMICAL REVIEWS, 1993, 93 (04) :1371-1448
[8]   Palladium catalysed coupling of imidazoles to alkynyl and vinyl substrates [J].
Cliff, MD ;
Pyne, SG .
TETRAHEDRON, 1996, 52 (43) :13703-13712
[9]   An enantioselective synthetic route to atractyligenin using the oxazaborolidine-catalyzed reduction of beta-silyl- or beta-stannyl-substituted alpha,beta-enones as a key step [J].
Corey, EJ ;
GuzmanPerez, A ;
Lazerwith, SE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (49) :11769-11776
[10]   USEFUL NEW ORGANOMETALLIC REAGENTS FOR SYNTHESIS OF ALLYLIC ALCOHOLS BY NUCLEOPHILIC VINYLATION [J].
COREY, EJ ;
WOLLENBERG, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (15) :2265-2266