On the Hydrostannylation of Aryl Propargylic Alcohols and Their Derivatives: Remarkable Differences in Both Regio‐ and Stereoselectivity in Radical‐ and Nonradical‐Mediated Transformations |
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Authors: | Dr. Martins S. Oderinde Dr. Robert D. J. Froese Prof. Michael G. Organ |
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Affiliation: | 1. Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3 (Canada);2. The Dow Chemical Company, Midland, Michigan, 48674 (USA) |
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Abstract: | Herein, we describe a highly regio‐ and stereoselective radical‐mediated and molecular‐oxygen (O2)‐dependent hydrostannylation of phenyl propargylic alcohols and their derivatives. There is a significant steric effect on the stereoselectivity of the tin‐radical addition. Further, the uncatalyzed regio‐ and stereoselective hydrostannylation of aryl propargylic alcohols with nBu3SnH and Ph3SnH is also described and occurs with near titration kinetics. Although the uncatalyzed addition with nBu3SnH gave a remarkable γ‐regioselectivity irrespective of the electronic nature of the aryl moiety, addition with Ph3SnH appears to be driven by the electronic nature of the aryl alkynes. |
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Keywords: | hydrostannylation radicals regioselectivity stereoselectivity vinylstannane |
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