Yazdani, Sima; Junor, Glen P.; Peltier, Jesse L.; Gembicky, Milan; Jazzar, Rodolphe; Grotjahn, Douglas B.; Bertrand, Guy (2020). Data from: Influence of Carbene and Phosphine Ligands on the Catalytic Activity of Gold Complexes in the Hydroamination and Hydrohydrazination of Alkynes. UC San Diego Library Digital Collections. Dataset. https://doi.org/10.6075/J0GB22FN

ABSTRACT: Through kinetic measurements, catalytic and stoichiometric experiments, as well as DFT calculations, we compare the catalytic activity of gold complexes supported by a variety of ligands (R3P, NHC, CAAC-5, CAAC-6, BiCAAC) in the hydroamination and hydro-hydrazination 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 able to compete with sophisticated state-of-the-art phosphine and NHC ligands, which feature secondary interaction capabilities.

• 2019 to 2020

• 2020

• Gembicky, Milan
• Junor, Glen P.
• Peltier, Jesse L.
• Yazdani, Sima

• Bertrand, Guy

• Grotjahn, Douglas B.
• Jazzar, Rodolphe

Gaussian 09, Revision D.01,M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2013.

This work was supported at UCSD by the U.S. Department of Energy, Office of Science, Basic Energy Sciences, Catalysis Science Program, under Award No. DE-SC0009376 (GB). At SDSU, experimental work was supported by NSF award CHE-1800598 (D.B.G.), and by a SDSU University Graduate Fellowship (S.Y.). Thanks are due to the Alfred P. Sloan Foundations University Centre for Exemplary Mentoring (G.P.J.). This material is based upon work supported by the National Science Foundation Graduate Research Fellowship Program under Grant No. (DGE-1650112; G.P.J. and J. L. P.). Any opinions, findings, and conclusions or recommendations expressed in this material are those of the author(s) and do not necessarily reflect the views of the National Science Foundation. We also acknowledge the Keck Foundation for provided computational resources.

• Carbenes
• Density functional theory
• Gold catalysis
• Hydroamination

• data

• No linguistic content; Not applicable

Doi: https://doi.org/10.6075/J0GB22FN

Primary associated publication

• Yazdani, Sima; Junor, Glen P.; Peltier, Jesse L.; Gembicky, Milan; Jazzar, Rodolphe; Grotjahn, Douglas B.; Bertrand, Guy (2020). Influence of Carbene and Phosphine Ligands on the Catalytic Activity of Gold Complexes in the Hydroamination and Hydrohydrazination of Alkynes. ACS Catal. 2020, 10, 5190-5201. https://doi.org/10.1021/acscatal.0c01352

Software

• Gaussian: http://gaussian.com/glossary/g09/

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2023-06-06