Synlett 2021; 32(07): 679-684
DOI: 10.1055/a-1345-3491
letter

Porphyrin-Catalyzed Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones

Ao Li
a   College of Chemistry and Environmental Engineering, Sichuan University of Science and Engineering, Zigong 643000, P. R. of China
,
Bin Pan
b   College of Pharmacy, Third Military Medical University, Chongqing 400038, P. R. of China
,
Chao Mu
a   College of Chemistry and Environmental Engineering, Sichuan University of Science and Engineering, Zigong 643000, P. R. of China
,
Na Wang
b   College of Pharmacy, Third Military Medical University, Chongqing 400038, P. R. of China
,
Yu-Long Li
a   College of Chemistry and Environmental Engineering, Sichuan University of Science and Engineering, Zigong 643000, P. R. of China
,
Qin Ouyang
b   College of Pharmacy, Third Military Medical University, Chongqing 400038, P. R. of China
› Author Affiliations

The National Key R&D program of China (2018YFA0507900), the Chongqing Young Top Talents Training Plan, Chongqing Postdoctoral Innovation Project Funding (cstc2019jcyj-bsh0019), and Sichuan Provincial Human Resource and Social Security Department.


Abstract

A visible-light-induced direct α-oxygenation of N-substituted 1,2,3,4-tetrahydroisoquinoline derivatives has been successfully developed. Tetraphenylporphyrinatozinc(II) has been identified as an effective and inexpensive photocatalyst for this transformation with a wide range of substrates. This protocol provides a convenient route to the desired products in moderate to good yields at room temperature under air.

Supporting Information



Publication History

Received: 03 December 2020

Accepted after revision: 04 January 2021

Accepted Manuscript online:
04 January 2021

Article published online:
18 January 2021

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