The reaction of porphyrins with α,β-acetylenic ketone/ester (Morita-Baylis-Hiliman) promoted by MgI2 and subsequent Sonogashira coupling reactions

被引：9

作者：

Ahmed, Naseem ^{[1
]}

Ali, Hasrat ^{[1
]}

van Lier, Johan E. ^{[1
]}

机构：

[1] Univ Sherbrooke, Fac Med & Hlth Sci, Dept Med Nucl & Radiobiol, Sherbrooke, PQ J1H 5N4, Canada

来源：

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES | 2006年 / 10卷 / 9-10期

关键词：

porphyrin aldehydes; MBH adducts; MgI2; alpha; beta-acetylenic ketone/ester; Dess-Martin periodinane; Pd-catalyst; Sonogashira coupling;

D O I：

10.1142/S1088424606000533

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The stereoselective synthesis of (Z)-beta-iodovinyl ketones/esters of Morita-Baylis-Hillman (MBH) porphyrin adducts has been achieved with a tandem formation of C-C and C-I bonds in a three-component reaction. The reaction is promoted by MgI2 as a Lewis acid, as well as an iodine source for a Michael-type addition. The MBH adducts are efficiently oxidized to the corresponding ketones with Dess-Martin periodinane (DMP). These scaffolds are further used in a palladium-catalyzed Sonogashira carbon-carbon coupling reaction to obtain highly extended porphyrin systems. Copyright (c) 2006 Society of Porphyrins & Phthalocyanines.

引用

页码：1172 / 1178

页数：7

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