Diastereoselective 1,2-difunctionalization of 1,3-enynes enabled by merging photoexcited Hantzsch ester with chromium catalysis

Abstract

1,3-Enynes have been widely recognized as a prevalent synthon for the construction of valuable allenes, 1,3-dienes, and propargylic derivatives. However, significant advancements have primarily focused on elucidating the ionic reaction...

1,3-Butadiene Dicarbofunctionalization Enabled by the Dual Role of Diaryl Ketone in Photo-HAT/Chromium Catalysis

“…Among the reactions, the three-component Nozaki–Hiyama–Kishi (NHK) type reactions involving radical precursors, conjugate olefins, and aldehydes are attractive, as they allow the rapid build-up of molecular complexity and the construction of two C­(sp 3 )–C­(sp 3 ) bonds with the concomitant introduction of highly valuable and versatile allyl and hydroxyl functionalities. In this context, Takai, Zhang, Glorious, Wang, Shi, and Li have made significant progress with alkyl halides, Hantzsch esters, organotrifluoroborates, and N -(acyloxy)­phthalimides (NHPI esters) as radical precursors based on stoichiometric CrCl 2 , metal reductant, or photoredox catalysis, with fluoroalkyls and alkyls incorporated into the final products. Nevertheless, the photo-hydrogen atom transfer (HAT)/chromium catalysis-enabled NHK type reaction is less developed.…”