We have developed visible-light-induced -hydroboration of diaryl alkynes via direct photoexcitation of in-situ-generated diboron complexes, affording previously elusive ()-1,2-diaryl-vinylboronates with high stereoselectivity. Experimental, spectroscopic, and theoretical mechanistic studies revealed that the triplet-state borate complex facilitates B-B bond cleavage and the desired C-B bond formation. This methodology does not require any catalyst and is operationally simple. The highly borylated 1,2-diaryl alkenes [1-(2-borylphenyl)vinyl)boronates] are shown to be useful as building blocks.
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http://dx.doi.org/10.1021/acs.orglett.4c00268 | DOI Listing |
Org Lett
March 2024
Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8550, Japan.
We have developed visible-light-induced -hydroboration of diaryl alkynes via direct photoexcitation of in-situ-generated diboron complexes, affording previously elusive ()-1,2-diaryl-vinylboronates with high stereoselectivity. Experimental, spectroscopic, and theoretical mechanistic studies revealed that the triplet-state borate complex facilitates B-B bond cleavage and the desired C-B bond formation. This methodology does not require any catalyst and is operationally simple.
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