Palladium-mediated fragmentation of meta photocycloadducts using carbon based electrophiles.: Part 1

被引：12
|
作者：
Penkett, CS [1 ]
Sims, RO
Byrne, PW
Kingston, L
French, R
Dray, L
Berritt, S
Lai, J
Avent, AG
Hitchcock, PB
机构：
[1] Univ Sussex, Dept Chem, Brighton BN1 9QJ, E Sussex, England
[2] Tocris Cookson Ltd, Bristol BS11 8TA, Avon, England
[3] AstraZeneca R&D Charnwood, Loughborough LE11 5RH, Leics, England
来源：
TETRAHEDRON | 2006年 / 62卷 / 14期
基金：
英国工程与自然科学研究理事会;
关键词：
photoaddition; palladium; Heck reaction; tandem reaction; atom efficiency; allylsilane formation;
D O I：
10.1016/j.tet.2006.01.042
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Substituted benzene derived meta photocycloadducts have been shown to undergo a fragmentation/arylation reaction under Heck reaction conditions to give bridged bicyclo[3.2.1] compounds in a highly atom-efficient manner. When an anisole derived meta photocycloadduct is used, a bridgehead ketone is generated. However, if an alkylbenzene derived meta photocycloadduct is used, a bridgehead alkene is formed. This strategy has been used to create novel enol ether and transient allyl silane compounds. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3423 / 3434
页数：12
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