Flash Communication: Cobalt-Catalyzed Asymmetric Hydrogenation of a Fluorinated Cyclobutenoic Acid Derivative

Katherine L. Moffa; Lauren N. Mendelsohn; Connor S. MacNeil; Matthew V. Pecoraro; Ian W. Davies; David K. Leahy; Paul J. Chirik

doi:10.1021/acs.organomet.5c00366

Flash Communication: Cobalt-Catalyzed Asymmetric Hydrogenation of a Fluorinated Cyclobutenoic Acid Derivative

Katherine L. Moffa
, Lauren N. Mendelsohn
, Connor S. MacNeil
, Matthew V. Pecoraro
, Ian W. Davies
, David K. Leahy
, Paul J. Chirik

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

An enantioselective hydrogenation of a fluorinated cyclobutenoic acid derivative using both neutral cobalt(II) and cationic, bis(phosphine)-supported cobalt(I) precatalysts has been developed. With 2 mol % of [((S,S)-^PhBPE)Co(η⁶-PhMe)][BAr^F₄], complete conversion and >99% ee was obtained at ambient temperature, enabling a route for the preparation of an enantioenriched bis(difluoro)-substituted cyclobutane. Deuterium-labeling studies supported homolytic cleavage of H₂and established the unsaturated starting material was not isomerized under catalytic hydrogenation conditions.

Original language	English (US)
Pages (from-to)	2516-2519
Number of pages	4
Journal	Organometallics
Volume	44
Issue number	21
DOIs	https://doi.org/10.1021/acs.organomet.5c00366
State	Published - Nov 10 2025

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1021/acs.organomet.5c00366

Cite this

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title = "Flash Communication: Cobalt-Catalyzed Asymmetric Hydrogenation of a Fluorinated Cyclobutenoic Acid Derivative",

abstract = "An enantioselective hydrogenation of a fluorinated cyclobutenoic acid derivative using both neutral cobalt(II) and cationic, bis(phosphine)-supported cobalt(I) precatalysts has been developed. With 2 mol \% of [((S,S)-PhBPE)Co(η6-PhMe)][BArF4], complete conversion and >99\% ee was obtained at ambient temperature, enabling a route for the preparation of an enantioenriched bis(difluoro)-substituted cyclobutane. Deuterium-labeling studies supported homolytic cleavage of H2and established the unsaturated starting material was not isomerized under catalytic hydrogenation conditions.",

author = "Moffa, \{Katherine L.\} and Mendelsohn, \{Lauren N.\} and MacNeil, \{Connor S.\} and Pecoraro, \{Matthew V.\} and Davies, \{Ian W.\} and Leahy, \{David K.\} and Chirik, \{Paul J.\}",

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doi = "10.1021/acs.organomet.5c00366",

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T2 - Cobalt-Catalyzed Asymmetric Hydrogenation of a Fluorinated Cyclobutenoic Acid Derivative

AU - Moffa, Katherine L.

AU - Mendelsohn, Lauren N.

AU - MacNeil, Connor S.

AU - Pecoraro, Matthew V.

AU - Davies, Ian W.

AU - Leahy, David K.

AU - Chirik, Paul J.

PY - 2025/11/10

Y1 - 2025/11/10

N2 - An enantioselective hydrogenation of a fluorinated cyclobutenoic acid derivative using both neutral cobalt(II) and cationic, bis(phosphine)-supported cobalt(I) precatalysts has been developed. With 2 mol % of [((S,S)-PhBPE)Co(η6-PhMe)][BArF4], complete conversion and >99% ee was obtained at ambient temperature, enabling a route for the preparation of an enantioenriched bis(difluoro)-substituted cyclobutane. Deuterium-labeling studies supported homolytic cleavage of H2and established the unsaturated starting material was not isomerized under catalytic hydrogenation conditions.

AB - An enantioselective hydrogenation of a fluorinated cyclobutenoic acid derivative using both neutral cobalt(II) and cationic, bis(phosphine)-supported cobalt(I) precatalysts has been developed. With 2 mol % of [((S,S)-PhBPE)Co(η6-PhMe)][BArF4], complete conversion and >99% ee was obtained at ambient temperature, enabling a route for the preparation of an enantioenriched bis(difluoro)-substituted cyclobutane. Deuterium-labeling studies supported homolytic cleavage of H2and established the unsaturated starting material was not isomerized under catalytic hydrogenation conditions.

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JF - Organometallics

IS - 21

ER -

Flash Communication: Cobalt-Catalyzed Asymmetric Hydrogenation of a Fluorinated Cyclobutenoic Acid Derivative

Abstract

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