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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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Publication details

The article was received on 11 Aug 2016, accepted on 26 Sep 2016 and first published on 27 Sep 2016


Article type: Research Article
DOI: 10.1039/C6QO00453A
Citation: Org. Chem. Front., 2016,3, 1691-1698
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    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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