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Reductive alkene formations

Name Reactions


Bamford-Stevens Reaction


Shapiro Reaction


Recent Literature


Triflic acid and a silane serve as a cooperative reductant for a deoxygenative transformation of ketones into alkenes. The reaction generates carbocations, that undergo β-H elimination much faster than hydride transfer from silane to produce alkenes with high selectivity.
J. Hou, X. Han, Y. Zhang, J. Huang, J. Wang, K. Yuan, Org. Lett., 2023, 25, 5709-5713.


Rhodium-catalyzed deoxygenations and borylations of ketones with B2pin2 provide alkenes, vinylboronates, and vinyldiboronates. These reactions offer mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates.
L. Tao, X. Guo, J. Li, R. Li, Z. Lin, W. Zhao, J. Am. Chem. Soc., 2020, 142, 18118-18127.