Direct sp3 C–H bond arylation, alkylation, and amidation of tetrahydroisoquinolines mediated by hypervalent iodine(III) under mild conditions

Wataru Muramatsu; Kimihiro Nakano; Chao-Jun Li

doi:10.1039/C3OB42354A

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Direct sp³ C–H bond arylation, alkylation, and amidation of tetrahydroisoquinolines mediated by hypervalent iodine(iii) under mild conditions†

Wataru Muramatsu,*^a Kimihiro Nakano^a and Chao-Jun Li*^b

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* Corresponding authors

^a Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki, Nagasaki 852-8521, Japan
E-mail: muramatu@nagasaki-u.ac.jp

^b Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC H3A 0B8, Canada
E-mail: cj.li@mcgill.ca

Abstract

We have developed a method for the sp³ C–H bond functionalization of tetrahydroisoquinolines (THIQs) mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA). The treatment of the THIQs with various nucleophiles in the presence of PIFA in a green solvent alternative gave the coupled products, with a C–C, C–N, or quaternary carbon center in high yields.

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Article information

DOI: https://doi.org/10.1039/C3OB42354A
Article type: Communication
Submitted: 25 Nov 2013
Accepted: 23 Jan 2014
First published: 05 Mar 2014

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Org. Biomol. Chem., 2014,12, 2189-2192

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Direct sp³ C–H bond arylation, alkylation, and amidation of tetrahydroisoquinolines mediated by hypervalent iodine(III) under mild conditions

W. Muramatsu, K. Nakano and C. Li, Org. Biomol. Chem., 2014, 12, 2189 DOI: 10.1039/C3OB42354A

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Organic & Biomolecular Chemistry