Highly practical copper(I)/TEMPO catalyst system for chemoselective aerobic oxidation of primary alcohols

Jessica M. Hoover, Shannon S. Stahl

Research output: Contribution to journalArticlepeer-review

673 Scopus citations

Abstract

Aerobic oxidation reactions have been the focus of considerable attention, but their use in mainstream organic chemistry has been constrained by limitations in their synthetic scope and by practical factors, such as the use of pure O 2 as the oxidant or complex catalyst synthesis. Here, we report a new (bpy)Cu I/TEMPO catalyst system that enables efficient and selective aerobic oxidation of a broad range of primary alcohols, including allylic, benzylic, and aliphatic derivatives, to the corresponding aldehydes using readily available reagents, at room temperature with ambient air as the oxidant. The catalyst system is compatible with a wide range of functional groups and the high selectivity for 1° alcohols enables selective oxidation of diols that lack protecting groups.

Original languageEnglish (US)
Pages (from-to)16901-16910
Number of pages10
JournalJournal of the American Chemical Society
Volume133
Issue number42
DOIs
StatePublished - Oct 26 2011
Externally publishedYes

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