Benzylic bromination catalyzed by triphenylphosphine selenide via Lewis basic activation

被引：4

作者：

Ayonon, Arianna ^{[1
]}

Nalbandian, Christopher ^{[1
]}

Guillemard, Lucas ^{[1
]}

Gustafson, Jeffrey ^{[1
]}

机构：

[1] San Diego State Univ, Dept Chem & Biochem, 5500 Campanile Dr, San Diego, CA 92102 USA

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 30期

关键词：

Triphenylphosphine selenide; Benzyl bromides; Phthalides; Lewis base catalysis; BOND-DISSOCIATION ENERGIES; N-BROMOSUCCINIMIDE; CHLORINATION; HETEROCYCLES; PHTHALIDES; ALCOHOLS; MILD;

D O I：

10.1016/j.tetlet.2017.06.042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of benzyl bromides was achieved under mild reaction conditions using N-bromosuccinimide as a bromine source and triphenylphosphine selenide as a catalyst. These conditions were compatible with a variety of substrates including boronic esters, protected amines to give imines, and carboxylic acids (to give phthalides when ortho to the benzylic center). A preliminary mechanistic investigation utilizing calculated bond dissociation energies (BDE) is employed to rationalize how a Lewis base can activate a radical mechanism. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：2940 / 2943

页数：4

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