Photosensitized [2+2]-Cycloadditions of Alkenylboronates and Alkenes

Yanyao Liu; Dongshun Ni; Bernard G Stevenson; Vikrant Tripathy; Sarah E Braley; Krishnan Raghavachari; John R Swierk; M Kevin Brown

doi:10.1002/anie.202200725

Photosensitized [2+2]-Cycloadditions of Alkenylboronates and Alkenes

Angew Chem Int Ed Engl. 2022 Jun 20;61(25):e202200725. doi: 10.1002/anie.202200725. Epub 2022 Apr 21.

Authors

Yanyao Liu¹, Dongshun Ni¹, Bernard G Stevenson², Vikrant Tripathy¹, Sarah E Braley¹, Krishnan Raghavachari¹, John R Swierk², M Kevin Brown¹

Affiliations

¹ Department of Chemistry, Indiana University, 800 E. Kirkwood Ave., Bloomington, IN 47401, USA.
² Department of Chemistry, Binghamton University, 4400 Vestal Parkway East, Binghamton, NY 13902, USA.

Abstract

A new strategy for the synthesis of highly versatile cyclobutylboronates via the photosensitized [2+2]-cycloaddition of alkenylboronates and alkenes is presented. The process is mechanistically different from other processes in that energy transfer occurs with the alkenylboronate as opposed to the other alkene. This strategy allows for the synthesis of an array of diverse cyclobutylboronates. The conversion of these adducts to other compounds as well as their utility in the synthesis of melicodenine C is demonstrated.

Abstract

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