Carbopalladation of bromoene-alkynylsilanes: mechanistic insights and synthesis of fused-ring bicyclic silanes and phenols

被引：14

作者：

Cordonnier, Marie-Caroline A. ^{[1
]}

Kan, S. B. Jennifer ^{[2
]}

Gockel, Birgit ^{[1
]}

Goh, Shermin S. ^{[1
]}

Anderson, Edward A. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England

[2] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

ORGANIC CHEMISTRY FRONTIERS | 2014年 / 1卷 / 06期

基金：

英国工程与自然科学研究理事会;

关键词：

CROSS-COUPLING REACTION; ANION CAPTURE PROCESSES; CASCADE CYCLIZATION; CATALYZED SYNTHESIS; ORGANIC-SYNTHESIS; GOLD CATALYSIS; PALLADIUM; CYCLOCARBOPALLADATION; CYCLOADDITION; 4-EXO-DIG;

D O I：

10.1039/c4qo00123k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed cascade cyclization of silylated bromoenynes and alkenylstannanes provides a straightforward route to a range of bicyclic silylated cyclohexadienes. Mechanistic insights into aspects of carbopalladation and unusual palladium-mediated isomerizations have been obtained through the detection of reaction intermediates, the isolation of byproducts, and reaction monitoring by VT NMR spectroscopy. The utility of the bicyclic products is illustrated through oxidation to bicyclic enones and phenols.

引用

页码：661 / 673

页数：13

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