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四种成分的自由基双官能化(RDD)反应:通过醛和叔丁基过氧化氢(TBHP)对两种不同烯烃的双官能化反应——β,δ-官能化酮的简便获得方法。

Four-Component Radical Dual Difunctionalization (RDD) of Two Different Alkenes with Aldehydes and -Butyl Hydroperoxide (TBHP): An Easy Access to β,δ-Functionalized Ketones.

机构信息

Key Laboratory for Green Organic Synthesis and Application of Hunan Province, College of Chemistry , Xiangtan University , Hunan 411105 , P. R. China.

Xiangya School of Pharmaceutical Sciences , Central South University , Hunan 410013 , P. R. China.

出版信息

Org Lett. 2019 Aug 2;21(15):6117-6121. doi: 10.1021/acs.orglett.9b02264. Epub 2019 Jul 19.

Abstract

A convenient Fe-catalyzed four-component radical dual difunctionalization and ordered assembly of two alkenes with aromatic/aliphatic aldehydes and TBHP to provide chain elongated β,δ-functionalized ketones via a one-pot procedure has been developed. Aldehydes were homolytically cleavaged to produce acyl radicals and subsequently allowed for the successive construction of C(sp)-C(sp), C(sp)-C(sp), and C(sp)-O bonds via dual radical insertions and radical-radical coupling, following the intrinsic nucleo/electrophilic reactivity of both the radicals and alkenes.

摘要

一种方便的 Fe 催化的四组分自由基双官能化和两个烯烃与芳香/脂肪醛和 TBHP 的有序组装,通过一锅法提供了通过链延长β,δ-官能化酮。醛通过均裂裂解产生酰基自由基,随后通过双自由基插入和自由基-自由基偶联,在自由基和烯烃的固有亲核/亲电性反应性的作用下,连续构建 C(sp)-C(sp)、C(sp)-C(sp)和 C(sp)-O 键。

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