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Overcoming product inhibition in catalysis of the intramolecular Schmidt reaction.

ABSTRACT: A method for carrying out the intramolecular Schmidt reaction of alkyl azides and ketones using a substoichiometric amount of catalyst is reported. Following extensive screening, the use of the strong hydrogen-bond-donating solvent hexafluoro-2-propanol was found to be consistent with low catalyst loadings, which ranged from 2.5 mol % for favorable substrates to 25 mol % for more difficult cases. Reaction optimization, broad substrate scope, and preliminary mechanistic studies of this improved version of the reaction are described.

SUBMITTER: Motiwala HF

PROVIDER: S-EPMC3921892 | biostudies-literature | 2013 Jun

REPOSITORIES: biostudies-literature

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Overcoming product inhibition in catalysis of the intramolecular Schmidt reaction.

Motiwala Hashim F HF Fehl Charlie C Li Sze-Wan SW Hirt Erin E Porubsky Patrick P Aubé Jeffrey J

Journal of the American Chemical Society 20130607 24

A method for carrying out the intramolecular Schmidt reaction of alkyl azides and ketones using a substoichiometric amount of catalyst is reported. Following extensive screening, the use of the strong hydrogen-bond-donating solvent hexafluoro-2-propanol was found to be consistent with low catalyst loadings, which ranged from 2.5 mol % for favorable substrates to 25 mol % for more difficult cases. Reaction optimization, broad substrate scope, and preliminary mechanistic studies of this improved v ...[more]

PMID: 23687993

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