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Highly stereoselective synthesis of (E)- and (Z)-alpha-fluoro-alpha,beta-unsaturated esters and (E)- and (Z)-alpha-fluoro-alpha,beta-unsaturated amides from 1-bromo-1-fluoroalkenes via palladium-catalyzed carbonylation reactions.通过钯催化的羰基化反应，从1-溴-1-氟烯烃高度立体选择性地合成（E）-和（Z）-α-氟-α，β-不饱和酯以及（E）-和（Z）-α-氟-α，β-不饱和酰胺。
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A facile and mild method for the synthesis of terminal bromofluoroolefins via diethylzinc-promoted Wittig reaction.一种通过二乙基锌促进的维蒂希反应合成末端溴氟烯烃的简便温和方法。
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8
Room-temperature Stille cross-couplings of alkenyltin reagents and functionalized alkyl bromides that possess beta hydrogens.具有β-氢的链烯基锡试剂与官能化烷基溴化物的室温施蒂勒交叉偶联反应。
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通过二卤代烯烃与溴化烷基锌的交叉偶联反应合成多取代卤代烯烃。

Synthesis of the multisubstituted halogenated olefins via cross-coupling of dihaloalkenes with alkylzinc bromides.

作者信息

Andrei Daniela, Wnuk Stanislaw F

机构信息

Department of Chemistry and Biochemistry, Florida International University, Miami, Florida 33199, USA.

出版信息

J Org Chem. 2006 Jan 6;71(1):405-8. doi: 10.1021/jo051980e.

DOI:10.1021/jo051980e
PMID:16388671
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2527053/
Abstract

[reaction: see text] The 1-fluoro-1-haloalkenes undergo Pd-catalyzed Negishi cross-couplings with primary alkylzinc bromides to give multisubstituted fluoroalkenes. The alkylation was trans-selective giving pure Z-fluoroalkenes in most cases. The highest yields were obtained with Pd2(dba)3 and PdCl2(dppb) catalysts but the best stereochemical outcome was obtained with less reactive Pd(PPh3)4. The tertiary alkylzincs also produced desired fluoroalkenes in high yields. Coupling of beta,beta-dichlorostyrene with organozinc reagent resulted in the formation of monocoupled product.

摘要

[反应：见正文] 1-氟-1-卤代烯烃与伯烷基溴化锌在钯催化下进行根岸交叉偶联反应，生成多取代氟烯烃。在大多数情况下，烷基化反应具有反式选择性，可得到纯的Z-氟烯烃。使用Pd2(dba)3和PdCl2(dppb)催化剂可获得最高产率，但使用活性较低的Pd(PPh3)4可得到最佳的立体化学结果。叔烷基锌也能高产率地生成所需的氟烯烃。β,β-二氯苯乙烯与有机锌试剂的偶联反应生成了单偶联产物。