Influence of Carbene and Phosphine Ligands on the Catalytic Activity of Gold Complexes in the Hydroamination and Hydrohydrazination of Alkynes

Yazdani, Sima; Junor, Glen P.; Peltier, Jesse L.; Gembicky, Milan; Jazzar, Rodolphe; Grotjahn, Douglas B.; Bertrand, Guy

doi:10.1021/acscatal.0c01352

Influence of Carbene and Phosphine Ligands on the Catalytic Activity of Gold Complexes in the Hydroamination and Hydrohydrazination of Alkynes

Journal Article · Tue Mar 31 00:00:00 EDT 2020 · ACS Catalysis

DOI:https://doi.org/10.1021/acscatal.0c01352· OSTI ID:1801903

^[1]; ^[2]; ^[2]; Gembicky, Milan ^[2]; ^[2]; Grotjahn, Douglas B. ^[3]; ^[2]

Univ. of California, San Diego, CA (United States); San Diego State Univ., CA (United States); OSTI
Univ. of California, San Diego, CA (United States)
San Diego State Univ., CA (United States)

Through kinetic measurements, catalytic and stoichiometric experiments, and DFT calculations, we compare the catalytic activity of gold complexes supported by a variety of ligands (R₃P, NHC, CAAC-5, CAAC-6, and BiCAAC) in the hydroamination and hydrohydrazination of alkynes. This study provides a rationale for the superior efficiency of a gold complex bearing a bicyclic (alkyl)(amino) carbene (BiCAAC). We demonstrate that this ligand motif, which is readily available, provides a durable gold catalyst that is able to compete with sophisticated state-of-the-art phosphine and NHC ligands, which feature secondary interaction capabilities.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of California, San Diego, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: SC0009376

OSTI ID:: 1801903

Journal Information:: ACS Catalysis, Journal Name: ACS Catalysis Journal Issue: 9 Vol. 10; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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CCDC 1983923: Experimental Crystal Structure Determination Sima, Yazdani,; P., Junor, Glen; L., Peltier, Jesse https://doi.org/10.5517/ccdc.csd.cc24lfjq The current record is supplemented by this dataset	dataset	January 2022
CCDC 1983924: Experimental Crystal Structure Determination Sima, Yazdani,; P., Junor, Glen; L., Peltier, Jesse https://doi.org/10.5517/ccdc.csd.cc24lfkr The current record is supplemented by this dataset	dataset	January 2022
CCDC 1983925: Experimental Crystal Structure Determination Sima, Yazdani,; P., Junor, Glen; L., Peltier, Jesse https://doi.org/10.5517/ccdc.csd.cc24lfls The current record is supplemented by this dataset	dataset	January 2022
CCDC 1983926: Experimental Crystal Structure Determination Sima, Yazdani,; P., Junor, Glen; L., Peltier, Jesse https://doi.org/10.5517/ccdc.csd.cc24lfmt The current record is supplemented by this dataset	dataset	January 2022
Data from: Influence of Carbene and Phosphine Ligands on the Catalytic Activity of Gold Complexes in the Hydroamination and Hydrohydrazination of Alkynes Yazdani, Sima; Junor, Glen P.; Peltier, Jesse L. https://doi.org/10.6075/j0gb22fn The current record is supplemented by this dataset	dataset	January 2020

Influence of Carbene and Phosphine Ligands on the Catalytic Activity of Gold Complexes in the Hydroamination and Hydrohydrazination of Alkynes

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