Photodecarboxylative benzylations of phthalimide in pH 7 buffer: a simple access to 3-arylmethyleneisoindolin-1-ones

被引：45

作者：

Belluau, Vincent ^{[1
]}

Noeureuil, Pierre ^{[2
]}

Ratzke, Elfrun ^{[1
]}

Skvortsov, Aleksei ^{[1
]}

Gallagher, Sonia ^{[2
]}

Motti, Cherri Ann ^{[3
]}

Oelgemoeller, Michael ^{[1
]}

机构：

[1] James Cook Univ, Sch Pharm & Mol Sci, Townsville, Qld 4811, Australia

[2] Dublin City Univ, Sch Chem Sci, Dublin 9, Ireland

[3] Australian Inst Marine Sci, Biomol Anal Facil, Townsville, Qld 4810, Australia

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 36期

基金：

爱尔兰科学基金会;

关键词：

Photodecarboxylation; Benzylation; Phthalimide; Photochemistry; Micro-photochemistry; Isoindolinones; ALPHA-KETO CARBOXYLATES; ONE-POT SYNTHESIS; PHOTOCHEMICAL DECARBOXYLATION; STEREOSELECTIVE-SYNTHESIS; N-ALKYLPHTHALIMIDES; CYCLIZATION; SPECTROSCOPY; ADDITIONS; ROUTE; ACIDS;

D O I：

10.1016/j.tetlet.2010.07.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photoadditions of phenylacetates to phthalimide in pH 7 buffer solution give the corresponding benzylated-hydroxyphthalimidines in moderate to high yields of up to 94%. In a micro-structured reactor, higher conversions and purities are achieved. With branched phenylacetates, photoaddition affords diastereoisomeric mixtures with low to moderate de values. Subsequent acid-catalyzed dehydration furnishes the corresponding 3-arylmethyleneisoindolin-1-ones in good to excellent yields and with high E-selectivities. Irradiation of the parent 3-phenylmethyleneisoindolin-1-one under oxidative conditions only leads to cis/trans-isomerization. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：4738 / 4741

页数：4

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