Organocatalytic approach for C(sp3)-H bond arylation, alkylation, and amidation of isochromans under facile conditions

Wataru Muramatsu; Kimihiro Nakano

doi:10.1021/ol5006399

Organocatalytic approach for C(sp3)-H bond arylation, alkylation, and amidation of isochromans under facile conditions

Org Lett. 2014 Apr 4;16(7):2042-5. doi: 10.1021/ol5006399. Epub 2014 Mar 27.

Authors

Wataru Muramatsu¹, Kimihiro Nakano

Affiliation

¹ Graduate School of Biomedical Sciences, Nagasaki University , 1-14 Bunkyo-machi, Nagasaki, Nagasaki 852-8521, Japan.

PMID: 24673439
DOI: 10.1021/ol5006399

Abstract

A new catalytic approach for the synthesis of isochroman derivatives via direct C(sp(3))-H bond arylation is described. The oxidation reaction with [bis(trifluoroacetoxy)iodo]benzene facilitates the regeneration of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in the C(sp(3))-H bond arylation of isochroman. The reaction conditions can also be used for alkyl Grignard reagents and amides to afford the corresponding isochroman derivatives.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation
Amides / chemistry
Benzoquinones / chemistry
Catalysis
Chromans / chemical synthesis*
Chromans / chemistry
Indicators and Reagents
Molecular Structure
Oxidation-Reduction
Stereoisomerism

Substances

Amides
Benzoquinones
Chromans
Indicators and Reagents
dichlorodicyanobenzoquinone