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Synlett 2021; 32(10): 993-998
DOI: 10.1055/a-1458-5785
letter

Visible-Light Photoredox-Catalyzed Decarboxylative α-tert-Butylation of C(sp3)–H Bonds of N-Aryltetrahydroisoquinolines with Pivalic Acid under Transition-Metal-Free Conditions

Li Sun
a   Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China
,
Yicheng Zhang
a   Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China
,
Jie Liu∗
a   Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China
,
Pinhua Li∗
a   Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. of China
b   Anhui Laboratory of Clean Catalytic Engineering, Anhui Laboratory of Functional Complexes for Materials Chemistry and Application, College of Chemical and Environmental Engineering, Anhui Polytechnic University, Wuhu, Anhui 241000, P. R. of China
› Author AffiliationsWe gratefully acknowledge financial support from the National Natural Science Foundation of China (21901081), the Young Talent Key Project of Anhui Province (170808J02), the Natural Science Foundation of Anhui Province (2008085QB90), and the Project of Anhui Provincial Education Department (KJ2015TD002).
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Abstract

A transition-metal-free visible-light photoredox-catalyzed decarboxylative alkylation of the benzylic C(sp3)–H bonds of N-aryltetrahydroisoquinolines is reported. The method tolerates various functional groups and proceeds smoothly without requiring a stoichiometric oxidant. A preliminary mechanistic study indicated that a radical process is involved in the reaction.

Key words

photoredox catalysis - decarboxylation - alkylation - tetrahydroisoquinolines - carboxylic acids - organocatalysis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1458-5785.
  • Supporting Information


Publication History

Received: 21 February 2021

Accepted after revision: 22 March 2021

Accepted Manuscript online:
22 March 2021

Article published online:
12 April 2021

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