Three‐Component Allylic Alkylation Reaction of α‐Diazo Ketones with Water and Allyl Carbonates for Construction of Homoallylic Alcohols

Abstract A three‐component allylic alkylation reaction of α‐diazo ketones, water and allyl carbonate under the cooperative catalysis of Rh 2 (OAc) 4 , Pd 2 (dba) 3 and Brønsted acid was disclosed. This method provides an expeditious access to α‐keto homoallylic alcohols in good to high yields. Contr...

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Published inAdvanced synthesis & catalysis
Main Authors Yin, Liping, Zhang, Xinyi, Wang, Baofan, He, Mingjin, Li, Yi, Wang, Shaozhen, Jing, Tongfei, Kang, Zhenghui
Format Journal Article
LanguageEnglish
Published 05.08.2024
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Summary:Abstract A three‐component allylic alkylation reaction of α‐diazo ketones, water and allyl carbonate under the cooperative catalysis of Rh 2 (OAc) 4 , Pd 2 (dba) 3 and Brønsted acid was disclosed. This method provides an expeditious access to α‐keto homoallylic alcohols in good to high yields. Controlled experiments support that the transformations proceed through cross‐interception of two active intermediates Pd‐allyl species and enol intermediates derived from oxonium ylides. Moreover, synthetic transformations of the generated products enable the creation of motifs enriched with dense functional groups, underscoring their potential as valuable building blocks.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202400364