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Short Paper | Regular issue | Vol 91, No. 5, 2015, pp.1028-1035
Published online, 2nd April, 2015
DOI: 10.3987/COM-15-13205
Organocatalytic Regioselective Three-Component, One-Pot Allylic Substitution of Morita-Baylis-Hillman Carbonates

Lin Jiang,* Jiang-Feng Zhou, Fei Li, Yong-Gen Li, Hong-Li Li, Yong-Ming Chuan, and Ming-Long Yuan*

*Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Engineering Research Center of Biopolymer Functional Materials, Yunnan Minzu University, 134 Yi Er Yi Avenue, Kunming, Yunnan, 650031, China


A Lewis base mediated three-component, one-pot allylic substitution reaction of Morita-Baylis-Hillman (MBH) carbonates with water and 1-phenyl-5-methylsulfonyltetrazole (PTSO2Me) has been developed. In the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO), a series of 1-phenyl-5-functionalized tetrazoles are prepared in moderate to excellent yield (40-97%). The key reaction mechanism is rationalized by the ipso-substitution of PTSO2Me with hydroxide which derives from deprotonation of water.