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Issue 12, 2016
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Rh(i)-Catalyzed coupling of 2-bromoethyl aryldiazoacetates with tertiary propargyl alcohols through carbene migratory insertion

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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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Supplementary files

Article information


Submitted
11 Aug 2016
Accepted
26 Sep 2016
First published
27 Sep 2016

Org. Chem. Front., 2016,3, 1691-1698
Article type
Research Article

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

Z. Liu, Y. Xia, S. Feng, Y. Zhang and J. Wang, Org. Chem. Front., 2016, 3, 1691 DOI: 10.1039/C6QO00453A

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