Concurrent Biocatalytic Oxidation and C–C Bond Formation via Gold Catalysis: One-Pot Alkynylation of   N-Alkyl Tetrahydroisoquinolines

Marcin Odachowski; Michael F. Greaney; Nicholas J. Turner

doi:10.1021/acscatal.8b03169

Concurrent Biocatalytic Oxidation and C–C Bond Formation via Gold Catalysis: One-Pot Alkynylation of N-Alkyl Tetrahydroisoquinolines

Marcin Odachowski, Michael F. Greaney, Nicholas J. Turner

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Abstract

A cross-dehydrogenative coupling process has been developed involving the enzymatic oxidation of tetrahydroisoquinolines (THIQ) together with gold-catalyzed C–C bond-formation. The transformation demonstrates the compatibility of gold-mediated chemocatalysis and monoamine oxidase biocatalysis which act co-operatively in one vessel. A range of N-alkyl THIQs were functionalized in this manner at C-(1) position in high yields.

Original language	English
Pages (from-to)	10032-10035
Journal	ACS Catalysis
Volume	8
Issue number	11
Early online date	21 Sept 2018
DOIs	https://doi.org/10.1021/acscatal.8b03169
Publication status	Published - 2 Nov 2018

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Manchester Institute of Biotechnology

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abstract = "A cross-dehydrogenative coupling process has been developed involving the enzymatic oxidation of tetrahydroisoquinolines (THIQ) together with gold-catalyzed C–C bond-formation. The transformation demonstrates the compatibility of gold-mediated chemocatalysis and monoamine oxidase biocatalysis which act co-operatively in one vessel. A range of N-alkyl THIQs were functionalized in this manner at C-(1) position in high yields.",

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N2 - A cross-dehydrogenative coupling process has been developed involving the enzymatic oxidation of tetrahydroisoquinolines (THIQ) together with gold-catalyzed C–C bond-formation. The transformation demonstrates the compatibility of gold-mediated chemocatalysis and monoamine oxidase biocatalysis which act co-operatively in one vessel. A range of N-alkyl THIQs were functionalized in this manner at C-(1) position in high yields.

AB - A cross-dehydrogenative coupling process has been developed involving the enzymatic oxidation of tetrahydroisoquinolines (THIQ) together with gold-catalyzed C–C bond-formation. The transformation demonstrates the compatibility of gold-mediated chemocatalysis and monoamine oxidase biocatalysis which act co-operatively in one vessel. A range of N-alkyl THIQs were functionalized in this manner at C-(1) position in high yields.

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ER -

Concurrent Biocatalytic Oxidation and C–C Bond Formation via Gold Catalysis: One-Pot Alkynylation of N-Alkyl Tetrahydroisoquinolines

Abstract

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