Synthesis of 2-nickela(II)oxetanes from nickel(0) and epoxides: Structure, reactivity, and a new mechanism of formation

Addison N. Desnoyer, Eric G. Bowes, Brian O. Patrick, Jennifer A. Love

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

2-Nickelaoxetanes have been frequently invoked as reactive intermediates in catalytic reactions of epoxides using nickel, but have never been isolated or experimentally observed in these transformations. Herein, we report the preparation of a series of well-defined nickelaoxetanes formed via the oxidative addition of nickel(0) with epoxides featuring ketones. The stereochemistry of the products is retained, which has not yet been reported for nickelaoxetanes. Theoretical calculations support a bimetallic ring-opening/closing pathway over a concerted oxidative addition. Initial reactivity studies of a nickelaoxetane demonstrated protonolysis, oxidatively induced reductive elimination, deoxygenation, and elimination reactions when treated with the appropriate reagents.

Original languageEnglish (US)
Pages (from-to)12748-12751
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number40
DOIs
StatePublished - Oct 14 2015

Fingerprint

Dive into the research topics of 'Synthesis of 2-nickela(II)oxetanes from nickel(0) and epoxides: Structure, reactivity, and a new mechanism of formation'. Together they form a unique fingerprint.

Cite this