Issue 50, 2024

One-pot C(sp3)–H difluoroalkylation of tetrahydroisoquinolines and isochromans via electrochemical oxidation and organozinc alkylation

Abstract

The C(sp3)–H difluoroalkylation for the introduction of carbonylated CF2 groups into tetrahydroisoquinolines (THIQs) and isochromans has been achieved by using electrochemical oxidation and organozinc alkylation. This one-pot process proceeded smoothly under transition-metal catalyst- and chemical oxidant-free conditions, and the desired products were obtained in good to high yields with a broad scope, except for N-Boc-THIQ. In addition, the gram-scale experiment successfully demonstrated the promising scalability. This is the first example of an electrochemical method for C(sp3)–H difluoroalkylation of amines and ethers.

Graphical abstract: One-pot C(sp3)–H difluoroalkylation of tetrahydroisoquinolines and isochromans via electrochemical oxidation and organozinc alkylation

Supplementary files

Article information

Article type
Communication
Submitted
28 avr. 2024
Accepted
28 mai 2024
First published
29 mai 2024

Chem. Commun., 2024,60, 6395-6398

One-pot C(sp3)–H difluoroalkylation of tetrahydroisoquinolines and isochromans via electrochemical oxidation and organozinc alkylation

K. Kamata, M. Kuriyama, H. Tahara, A. Nishikawa, K. Yamamoto, Y. Demizu and O. Onomura, Chem. Commun., 2024, 60, 6395 DOI: 10.1039/D4CC02033B

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