Rh(i)-Catalyzed coupling of 2-bromoethyl aryldiazoacetates with tertiary propargyl alcohols through carbene migratory insertion?

Organic Chemistry Frontiers Pub Date: 2016-09-27 DOI: 10.1039/C6QO00453A

Abstract

A Rh(I)-catalyzed cross-coupling of 2-bromoethyl aryldiazoacetates with tertiary propargyl alcohols has been successfully achieved. This reaction follows a reaction sequence which involves C–C bond cleavage, Rh(I) carbene formation, carbene migratory insertion and nucleophilic substitution to achieve the construction of C(sp2)–C(sp) and C–O bonds. The products feature both enyne and ketene acetal moieties, which have been widely used as building blocks in organic synthesis and polymer science.

Graphical abstract: Rh(i)-Catalyzed coupling of 2-bromoethyl aryldiazoacetates with tertiary propargyl alcohols through carbene migratory insertion
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