Tuning the reactivity of organotin(IV) by LiOH: allylation and propargylation of epoxides via redox transmetalation

被引:30
作者
Banerjee, M [1 ]
Roy, UK [1 ]
Sinha, P [1 ]
Roy, S [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Organomet & Catalysis Lab, Kharagpur 721302, W Bengal, India
关键词
organotin(IV); allylation; propargylation; transmetalation;
D O I
10.1016/j.jorganchem.2004.12.008
中图分类号
O61 [无机化学];
学科分类号
070301 [无机化学]; 081704 [应用化学];
摘要
In presence of catalytic Pd(0) or Pt(II), a reagent combination of SnCl2-LiOH promotes the reaction of organic halides and epoxides in dichloromethane leading to the regioselective formation of corresponding homoallyl and homopropargyl alcohols in good yields. This 2-carbon extension strategy adds to the repertoire of Barbier reactions via metal salts and reinforces views on the enhanced reactivity of organotin having -OH pendant. (c) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:1422 / 1428
页数:7
相关论文
共 31 条
[1]
Rhodium(I)-catalyzed carbonyl allenylation versus propargylation via redox transmetalation across tetragonal tin(II) oxide [J].
Banerjee, M ;
Roy, S .
ORGANIC LETTERS, 2004, 6 (13) :2137-2140
[2]
Palladium(0) catalyzed regioselective carbonyl propargylation across tetragonal tin(II) oxide via redox transmetallation [J].
Banerjee, M ;
Roy, S .
CHEMICAL COMMUNICATIONS, 2003, (04) :534-535
[3]
AN INVESTIGATION OF THE BASE HYDROLYSIS OF METHYL-TIN AND BUTYL-TIN TRICHLORIDE IN AQUEOUS-SOLUTION BY H-1 AND SN-119 NMR-SPECTROSCOPY [J].
BLUNDEN, SJ ;
HILL, R .
INORGANICA CHIMICA ACTA, 1990, 177 (02) :219-223
[4]
DENG DL, 1993, CHEM LETT, V4, P857
[5]
DENG DL, 1995, CHINESE J ORG CHEM, V15, P95
[6]
Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones [J].
Denmark, SE ;
Fu, JP .
CHEMICAL REVIEWS, 2003, 103 (08) :2763-2793
[7]
HYDRATED SIGMA-BONDED ORGANOMETALLIC CATIONS IN ORGANIC-SYNTHESIS .1. ALLYL-STANNATION, CROTYL-STANNATION, 1-METHYLALLYL-STANNATION, CYCLOHEX-2-ENYL-STANNATION, AND CINNAMYL-STANNATION OF CARBONYL-COMPOUNDS IN WATER [J].
FURLANI, D ;
MARTON, D ;
TAGLIAVINI, G ;
ZORDAN, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 341 (1-3) :345-356
[8]
GYLDENFELDT F, 1994, ORGANOMETALLICS, V13, P906
[9]
Remarkable electronic effect on rhodium-catalyzed carbonyl additions and conjugated additions with arylmetallic reagents [J].
Huang, TS ;
Meng, Y ;
Venkatraman, S ;
Wang, D ;
Li, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (30) :7451-7452
[10]
LEWIS ACID PROMOTED RING-OPENING ALLYLATION OF EPICHLOROHYDRIN WITH ALLYLIC SILANES AND STANNANES TO AFFORD 1-CHLORO-5-ALKEN-2-OLS - A SHORT SYNTHESIS OF (S)-(-)-IPSENOL [J].
IMAI, T ;
NISHIDA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (16) :4849-4852