Palladium-Catalyzed Asymmetric Synthesis of Allylic Fluorides

被引：151

作者：

Katcher, Matthew H. ^{[1
]}

Doyle, Abigail G. ^{[1
]}

机构：

[1] Princeton Univ, Dept Chem, Princeton, NJ 08544 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 49期

关键词：

BOND FORMATION; REDUCTIVE ELIMINATION; ENANTIOSELECTIVE FLUORINATION; NUCLEOPHILIC FLUORINATION; ARYL FLUORIDES; COMPLEXES; ALKYLATION; CHEMISTRY; STEREOCHEMISTRY; RUTHENIUM(II);

D O I：

10.1021/ja109120n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective fluorination of readily available cyclic allylic chlorides with AgF has been accomplished using a Pd(0) catalyst and Trost bisphosphine ligand. The reactions proceed with unprecedented ease of operation for Pd-mediated nucleophilic fluorination, allowing access to highly enantioenriched cyclic allylic fluorides that bear diverse functional groups. Evidence that supports a mechanism in which C F bond formation occurs by an S(N)2-type attack of fluoride on a Pd(II)-allyl intermediate is presented.

引用

页码：17402 / 17404

页数：3

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