Copper-catalyzed asymmetric sp3 C-H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

Pierre Querard; Inna Perepichka; Eli Zysman-Colman; Chao-Jun Li

doi:10.3762/bjoc.12.260

Copper-catalyzed asymmetric sp³ C-H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

Pierre Querard, Inna Perepichka, Eli Zysman-Colman, Chao-Jun Li

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

Abstract

This report describes a highly enantioselective oxidative sp³ C-H arylation of N-aryltetrahydroisoquinolines (THIQs) through a dual catalysis platform. The combination of the photoredox catalyst, [Ir(ppy)₂(dtbbpy)]PF₆, and chiral copper catalysts provide a mild and highly effective sp³ C-H asymmetric arylation of THIQs.

Original language	English
Pages (from-to)	2636-2643
Number of pages	8
Journal	Beilstein Journal of Organic Chemistry
Volume	12
DOIs	https://doi.org/10.3762/bjoc.12.260
Publication status	Published - 6 Dec 2016

Keywords

C-H arylation
Copper catalyst
Enantioselectivity
Visible light

Access to Document

10.3762/bjoc.12.260Licence: CC BY

Zysman-Colman_2016_BJOC_sp3C-HArlyation_CC
© 2016 Querard et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Final published version, 344 KBLicence: CC BY

Cite this

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title = "Copper-catalyzed asymmetric sp3 C-H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst",

abstract = "This report describes a highly enantioselective oxidative sp3 C-H arylation of N-aryltetrahydroisoquinolines (THIQs) through a dual catalysis platform. The combination of the photoredox catalyst, [Ir(ppy)2(dtbbpy)]PF6, and chiral copper catalysts provide a mild and highly effective sp3 C-H asymmetric arylation of THIQs.",

keywords = "C-H arylation, Copper catalyst, Enantioselectivity, Visible light",

author = "Pierre Querard and Inna Perepichka and Eli Zysman-Colman and Chao-Jun Li",

note = "We are grateful to the Canada Research Chair (Tier 1) foundation (to C.-J. Li), NSERC, CFI, and FQRNT (CCVC) for their support of our research.",

year = "2016",

month = dec,

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doi = "10.3762/bjoc.12.260",

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journal = "Beilstein Journal of Organic Chemistry",

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T1 - Copper-catalyzed asymmetric sp3 C-H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

AU - Querard, Pierre

AU - Perepichka, Inna

AU - Zysman-Colman, Eli

AU - Li, Chao-Jun

N1 - We are grateful to the Canada Research Chair (Tier 1) foundation (to C.-J. Li), NSERC, CFI, and FQRNT (CCVC) for their support of our research.

PY - 2016/12/6

Y1 - 2016/12/6

N2 - This report describes a highly enantioselective oxidative sp3 C-H arylation of N-aryltetrahydroisoquinolines (THIQs) through a dual catalysis platform. The combination of the photoredox catalyst, [Ir(ppy)2(dtbbpy)]PF6, and chiral copper catalysts provide a mild and highly effective sp3 C-H asymmetric arylation of THIQs.

AB - This report describes a highly enantioselective oxidative sp3 C-H arylation of N-aryltetrahydroisoquinolines (THIQs) through a dual catalysis platform. The combination of the photoredox catalyst, [Ir(ppy)2(dtbbpy)]PF6, and chiral copper catalysts provide a mild and highly effective sp3 C-H asymmetric arylation of THIQs.

KW - C-H arylation

KW - Copper catalyst

KW - Enantioselectivity

KW - Visible light

U2 - 10.3762/bjoc.12.260

DO - 10.3762/bjoc.12.260

M3 - Article

AN - SCOPUS:85008153150

SN - 1860-5397

VL - 12

SP - 2636

EP - 2643

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -