Thermodynamically leveraged tandem catalysis for ester RC(O)O-R′ bond hydrogenolysis. scope and mechanism

Tracy L. Lohr; Zhi Li; Rajeev S. Assary; Larry A. Curtiss; Tobin J. Marks

doi:10.1021/acscatal.5b00950

Thermodynamically leveraged tandem catalysis for ester RC(O)O-R′ bond hydrogenolysis. scope and mechanism

Tracy L. Lohr, Zhi Li, Rajeev S. Assary, Larry A. Curtiss, Tobin J. Marks^*

^*Corresponding author for this work

Chemistry

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

27 Scopus citations

Abstract

Rapid and selective formal hydrogenolysis of aliphatic ester RC(O)O-R′ linkages is achieved by a tandem homogeneous metal triflate + supported palladium catalytic system. The triflate catalyzes the mildly exothermic, turnover-limiting O-R′ cleavage process, whereas the exothermic hydrogenation of the intermediate alkene further drives the overall reaction to completion.

Original language	English (US)
Pages (from-to)	3675-3679
Number of pages	5
Journal	ACS Catalysis
Volume	5
Issue number	6
DOIs	https://doi.org/10.1021/acscatal.5b00950
State	Published - Jun 5 2015

Keywords

C-O cleavage
biomass
hydrogenolysis
metal triflates
tandem catalysis
thermodynamic leveraging

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1021/acscatal.5b00950

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title = "Thermodynamically leveraged tandem catalysis for ester RC(O)O-R′ bond hydrogenolysis. scope and mechanism",

abstract = "Rapid and selective formal hydrogenolysis of aliphatic ester RC(O)O-R′ linkages is achieved by a tandem homogeneous metal triflate + supported palladium catalytic system. The triflate catalyzes the mildly exothermic, turnover-limiting O-R′ cleavage process, whereas the exothermic hydrogenation of the intermediate alkene further drives the overall reaction to completion.",

keywords = "C-O cleavage, biomass, hydrogenolysis, metal triflates, tandem catalysis, thermodynamic leveraging",

author = "Lohr, \{Tracy L.\} and Zhi Li and Assary, \{Rajeev S.\} and Curtiss, \{Larry A.\} and Marks, \{Tobin J.\}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

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doi = "10.1021/acscatal.5b00950",

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T1 - Thermodynamically leveraged tandem catalysis for ester RC(O)O-R′ bond hydrogenolysis. scope and mechanism

AU - Lohr, Tracy L.

AU - Li, Zhi

AU - Assary, Rajeev S.

AU - Curtiss, Larry A.

AU - Marks, Tobin J.

PY - 2015/6/5

Y1 - 2015/6/5

N2 - Rapid and selective formal hydrogenolysis of aliphatic ester RC(O)O-R′ linkages is achieved by a tandem homogeneous metal triflate + supported palladium catalytic system. The triflate catalyzes the mildly exothermic, turnover-limiting O-R′ cleavage process, whereas the exothermic hydrogenation of the intermediate alkene further drives the overall reaction to completion.

AB - Rapid and selective formal hydrogenolysis of aliphatic ester RC(O)O-R′ linkages is achieved by a tandem homogeneous metal triflate + supported palladium catalytic system. The triflate catalyzes the mildly exothermic, turnover-limiting O-R′ cleavage process, whereas the exothermic hydrogenation of the intermediate alkene further drives the overall reaction to completion.

KW - C-O cleavage

KW - biomass

KW - hydrogenolysis

KW - metal triflates

KW - tandem catalysis

KW - thermodynamic leveraging

UR - https://www.scopus.com/pages/publications/84930675569

UR - https://www.scopus.com/inward/citedby.url?scp=84930675569&partnerID=8YFLogxK

U2 - 10.1021/acscatal.5b00950

DO - 10.1021/acscatal.5b00950

M3 - Article

AN - SCOPUS:84930675569

SN - 2155-5435

VL - 5

SP - 3675

EP - 3679

JO - ACS Catalysis

JF - ACS Catalysis

IS - 6

ER -

Thermodynamically leveraged tandem catalysis for ester RC(O)O-R′ bond hydrogenolysis. scope and mechanism

Abstract

Keywords

ASJC Scopus subject areas

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