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

Research output: Contribution to journal › Article › peer-review

242 Downloads (Pure)

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

Research Beacons, Institutes and Platforms

Manchester Institute of Biotechnology

Access to Document

10.1021/acscatal.8b03169

cs_2018_03169c_manuscipt_pureAccepted author manuscript, 819 KB

Cite this

@article{6dc2e3232cdc4060a1d20cf3072f72a5,

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

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.",

author = "Marcin Odachowski and Greaney, \{Michael F.\} and Turner, \{Nicholas J.\}",

year = "2018",

month = nov,

day = "2",

doi = "10.1021/acscatal.8b03169",

language = "English",

volume = "8",

pages = "10032--10035",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - Concurrent Biocatalytic Oxidation and C–C Bond Formation via Gold Catalysis: One-Pot Alkynylation of N-Alkyl Tetrahydroisoquinolines

AU - Odachowski, Marcin

AU - Greaney, Michael F.

AU - Turner, Nicholas J.

PY - 2018/11/2

Y1 - 2018/11/2

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.

UR - https://www.scopus.com/pages/publications/85054414215

U2 - 10.1021/acscatal.8b03169

DO - 10.1021/acscatal.8b03169

M3 - Article

SN - 2155-5435

VL - 8

SP - 10032

EP - 10035

JO - ACS Catalysis

JF - ACS Catalysis

IS - 11

ER -

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

Abstract

Research Beacons, Institutes and Platforms

Access to Document

Other files and links

Fingerprint

Cite this