铑催化的芳基硼酸酯和重氮酯的交叉偶联反应以及串联烷基化反应用于合成季铵盐 α,α-杂芳基羧酸酯。
Rhodium-catalyzed cross-coupling reaction of arylboronates and diazoesters and tandem alkylation reaction for the synthesis of quaternary α,α-heterodiaryl carboxylic esters.
机构信息
State Key Laboratory for Chirosciences, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong.
出版信息
Org Lett. 2011 Oct 7;13(19):5370-3. doi: 10.1021/ol2022577. Epub 2011 Sep 6.
PMID:21894953
Abstract
A rhodium-catalyzed one-pot three-component coupling reaction was developed for the synthesis of quaternary α,α-heterodiaryl carboxylic esters. This reaction involves cross-coupling of the arylrhodium(I) complexes with α-aryldiazoacetates to form oxa-π-allylrhodium complexes. With KOtBu and alkyl halides, tandem alkylation of the allyl complex occurs to form a quaternary stereocenter at the carbenic carbon.
摘要
发展了一种铑催化的一锅法三组分偶联反应，用于合成季铵盐α,α-杂芳基羧酸酯。该反应涉及芳基铑（I）配合物与α-芳基重氮乙酸酯的交叉偶联，形成氧杂-π-烯丙基铑配合物。用 KOtBu 和卤代烷烃，烯丙基配合物发生串联烷基化反应，在碳正离子上形成季碳立体中心。
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