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

https://doi.org/10.1021/acscatal.0c01352

Yazdani, Sima; Junor, Glen P.; Peltier, Jesse L.; Gembicky, Milan; Jazzar, Rodolphe; Grotjahn, Douglas B.; Bertrand, Guy (May 2020, ACS Catalysis)

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Toward Improving the Selectivity of Organic Halide Electrocarboxylation with Mechanistically Informed Solvent Selection

https://doi.org/10.1021/jacs.2c10561

Corbin, Nathan; Junor, Glen P.; Ton, Thu N.; Baker, Rachel J.; Manthiram, Karthish (January 2023, Journal of the American Chemical Society)
Stable Singlet Carbenes as Organic Superbases

https://doi.org/10.1002/anie.202111588

Vermersch, François; Yazdani, Sima; Junor, Glen P.; Grotjahn, Douglas B.; Jazzar, Rodolphe; Bertrand, Guy (November 2021, Angewandte Chemie International Edition)

Abstract A simple experimental procedure for scaling carbene Brønsted basicity is described. The results highlight the strong basicity of pyrazol‐4‐ylidenes, a type of mesoionic carbene, also named cyclic‐bentallenes (CBA). They are more basic (pK_aH>42.7 in acetonitrile) than the popular proazaphosphatrane Verkade bases, and even the Schwesinger phosphazene superbase P₄(^tBu). The basicity of these compounds can readily be tuned, and they are accessible in multigram quantities. These results open new avenues for carbon centered superbases.
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Cyclic (Alkyl)(amino)carbene Ligands Enable Cu‐Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes**

https://doi.org/10.1002/anie.202106107

Gao, Yang; Yazdani, Sima; Kendrick, IV, Aaron; Junor, Glen P.; Kang, Taeho; Grotjahn, Douglas B.; Bertrand, Guy; Jazzar, Rodolphe; Engle, Keary M. (July 2021, Angewandte Chemie International Edition)

Abstract Regioselective hydrofunctionalization of alkynes represents a straightforward route to access alkenyl boronate and silane building blocks. In previously reported catalytic systems, high selectivity is achieved with a limited scope of substrates and/or reagents, with general solutions lacking. Herein, we describe a selective copper‐catalyzed Markovnikov hydrofunctionalization of terminal alkynes that is facilitated by strongly donating cyclic (alkyl)(amino)carbene (CAAC) ligands. Using this method, both alkyl‐ and aryl‐substituted alkynes are coupled with a variety of boryl and silyl reagents with high α‐selectivity. The reaction is scalable, and the products are versatile intermediates that can participate in various downstream transformations. Preliminary mechanistic experiments shed light on the role of CAAC ligands in this process.
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