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Rhodium Catalyzed Synthesis of Benzopyrans via Transannulation of N-Sulfonyl-1,2,3-triazoles with 2-Hydroxybenzyl Alcohols. 2018
Department of Chemistry , Indian Institute of Technology Madras , Chennai 600036 , India.
An efficient and novel rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with in situ generated o-quinone methides ( o-QMs) from 2-hydroxybenzyl alcohols has been achieved for the synthesis of substituted benzopyrans in good yields. The developed reaction involves nucleophilic attack of o-QM to α-imino rhodium carbenoid to generate a carbonyl ylide followed by 6π-electrocyclization and isomerization. Furthermore, the utility of the methodology was demonstrated in the one-pot synthesis and construction of polyheteroaromatics.
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