Palladium-Catalyzed Formal Hydroalkylation of Aryl-Substituted Alkynes with Hydrazones |
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| Authors: | Lin Yu Dr Leiyang Lv Dr Zihang Qiu Dr Zhangpei Chen Prof Dr Ze Tan Dr Yu-Feng Liang Prof Dr Chao-Jun Li |
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| Institution: | 1. Department of Chemistry and FRQNT Center for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 0B8 Canada;2. Department of Chemistry and FRQNT Center for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 0B8 Canada
These authors contributed equally to this work.;3. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082 P. R. China |
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| Abstract: | We have developed an unprecedented Pd-catalyzed formal hydroalkylation of alkynes with hydrazones, which are generated in situ from naturally abundant aldehydes, as both alkylation reagents and hydrogen donors. The hydroalkylation proceeds with high regio- and stereoselectivity to form (Z)-alkenes, which are more difficult to generate compared to (E)-alkenes. The reaction is compatible with a wide range of functional groups, including hydroxy, ester, ketone, nitrile, boronic ester, amine, and halide groups. Furthermore, late-stage modifications of natural products and pharmaceutical derivatives exemplify its unique chemoselectivity, regioselectivity, and synthetic applicability. Mechanistic studies indicate the possible involvement of Pd-hydride intermediates. |
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| Keywords: | aldehydes alkenes alkynes hydrazones palladium |
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