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Mitsunobu Reactions Catalytic in Phosphine and a Fully Catalytic System.

ABSTRACT: The Mitsunobu reaction is renowned for its mild reaction conditions and broad substrate tolerance, but has limited utility in process chemistry and industrial applications due to poor atom economy and the generation of stoichiometric phosphine oxide and hydrazine by-products that complicate purification. A catalytic Mitsunobu reaction using innocuous reagents to recycle these by-products would overcome both of these shortcomings. Herein we report a protocol that is catalytic in phosphine (1-phenylphospholane) employing phenylsilane to recycle the catalyst. Integration of this phosphine catalytic cycle with Taniguchi's azocarboxylate catalytic system provided the first fully catalytic Mitsunobu reaction.

SUBMITTER: Buonomo JA

PROVIDER: S-EPMC4648044 | biostudies-literature | 2015 Oct

REPOSITORIES: biostudies-literature

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Mitsunobu Reactions Catalytic in Phosphine and a Fully Catalytic System.

Buonomo Joseph A JA Aldrich Courtney C CC

Angewandte Chemie (International ed. in English) 20150908 44

The Mitsunobu reaction is renowned for its mild reaction conditions and broad substrate tolerance, but has limited utility in process chemistry and industrial applications due to poor atom economy and the generation of stoichiometric phosphine oxide and hydrazine by-products that complicate purification. A catalytic Mitsunobu reaction using innocuous reagents to recycle these by-products would overcome both of these shortcomings. Herein we report a protocol that is catalytic in phosphine (1-phen ...[more]

PMID: 26347115

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