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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.

Authors:
 [1];  [1];  [2];  [2];  [1]
  1. Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
  2. Materials Science Division, Argonne National Laboratory, Argonne, Illinois 60439, United States
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). Institute for Atom-efficient Chemical Transformations (IACT)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1385857
DOE Contract Number:  
AC02-06CH11357
Resource Type:
Journal Article
Journal Name:
ACS Catalysis
Additional Journal Information:
Journal Volume: 5; Journal Issue: 6; Related Information: IACT partners with Argonne National Laboratory (lead); Brookhaven National Laboratory; Northwestern University; Purdue University; University of Wisconsin at Madison; Journal ID: ISSN 2155-5435
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; catalysis (homogeneous), catalysis (heterogeneous), biofuels (including algae and biomass), bio-inspired, materials and chemistry by design, synthesis (novel materials), synthesis (scalable processing)

Citation Formats

Lohr, Tracy L., Li, Zhi, Assary, Rajeev S., Curtiss, Larry A., and Marks, Tobin J. Thermodynamically Leveraged Tandem Catalysis for Ester RC(O)O–R' Bond Hydrogenolysis. Scope and Mechanism. United States: N. p., 2015. Web. doi:10.1021/acscatal.5b00950.
Lohr, Tracy L., Li, Zhi, Assary, Rajeev S., Curtiss, Larry A., & Marks, Tobin J. Thermodynamically Leveraged Tandem Catalysis for Ester RC(O)O–R' Bond Hydrogenolysis. Scope and Mechanism. United States. doi:10.1021/acscatal.5b00950.
Lohr, Tracy L., Li, Zhi, Assary, Rajeev S., Curtiss, Larry A., and Marks, Tobin J. Mon . "Thermodynamically Leveraged Tandem Catalysis for Ester RC(O)O–R' Bond Hydrogenolysis. Scope and Mechanism". United States. doi:10.1021/acscatal.5b00950.
@article{osti_1385857,
title = {Thermodynamically Leveraged Tandem Catalysis for Ester RC(O)O–R' Bond Hydrogenolysis. Scope and Mechanism},
author = {Lohr, Tracy L. and Li, Zhi and Assary, Rajeev S. and Curtiss, Larry A. and Marks, Tobin J.},
abstractNote = {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.},
doi = {10.1021/acscatal.5b00950},
journal = {ACS Catalysis},
issn = {2155-5435},
number = 6,
volume = 5,
place = {United States},
year = {2015},
month = {5}
}