Cobalt catalyzed practical hydroboration of terminal alkynes with time-dependent stereoselectivity

Jinglan Wen, Yahao Huang, Yu Zhang, Hansjörg Grützmacher and Peng Hu ()
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Jinglan Wen: Sun Yat-sen University
Yahao Huang: Sun Yat-sen University
Yu Zhang: Sun Yat-sen University
Hansjörg Grützmacher: Sun Yat-sen University
Peng Hu: Sun Yat-sen University

Nature Communications, 2024, vol. 15, issue 1, 1-10

Abstract: Abstract Stereodefined vinylboron compounds are important organic synthons. The synthesis of E−1-vinylboron compounds typically involves the addition of a B-H bond to terminal alkynes. The selective generation of the thermodynamically unfavorable Z-isomers remains challenging, necessitating improved methods. Here, such a proficient and cost-effective catalytic system is introduced, comprising a cobalt salt and a readily accessible air-stable CNC pincer ligand. This system enables the transformation of terminal alkynes, even in the presence of bulky substituents, with excellent Z-selectivity. High turnover numbers (>1,600) and turnover frequencies (>132,000 h−1) are achieved at room temperature, and the reaction can be scaled up to 30 mmol smoothly. Kinetic studies reveal a formal second-order dependence on cobalt concentration. Mechanistic investigations indicate that the alkynes exhibit a higher affinity for the catalyst than the alkene products, resulting in exceptional Z-selective performance. Furthermore, a rare time-dependent stereoselectivity is observed, allowing for quantitative conversion of Z-vinylboronate esters to the E-isomers.

Date: 2024
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DOI: 10.1038/s41467-024-46550-y

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