Work

Metal-Free Functionalization of N , N -Dialkylanilines via Temporary Oxidation to N , N -Dialkylaniline N -Oxides and Group Transfer

Year: 2014

Type: article

Abstract: A simple set of protocols for the controlled elaboration of anilines is reported allowing access to a diverse array of aminophenols, aminoarylsulfonates, alkylated anilines, and aminoanilines in 29-95% yield in a single laboratory operation from easily isolable, bench-stable N,N-dialkylaniline N-oxides. The introduction of new C-O, C-C, and C-N bonds on the aromatic ring is made possible by a temporary increase in oxidation level and excision of a weak N-O bond.

Source: Organic Letters

DOI: 10.1021/ol501813s

Authors: Robert S. Lewis, Michael F. Wisthoff, J. Grissmerson, William J. Chain

Institutions: University of Hawaiʻi at Mānoa, University of Hawaii Cancer Center

Language: Hebrew

Topic: Oxidative Organic Chemistry Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Achievement Rewards for College Scientists Foundation, National Institutes of Health, University of California, Irvine, National Cancer Institute