94444-18-5Relevant academic research and scientific papers
Hydrogenation of alkenes via cooperative hydrogen atom transfer
Kattamuri, Padmanabha V.,West, Julian G.
supporting information, p. 19316 - 19326 (2020/11/13)
Radical hydrogenation via hydrogen atom transfer (HAT) to alkenes is an increasingly important transformation for the formation of thermodynamic alkane isomers. Current single-catalyst methods require stoichiometric oxidant in addition to hydride (H-) source to function. Here we report a new approach to radical hydrogenation: cooperative hydrogen atom transfer (cHAT), where each hydrogen atom donated to the alkene arrives from a different catalyst. Further, these hydrogen atom (H?) equivalents are generated from complementary hydrogen atom precursors, with each alkane requiring one hydride (H-) and one proton (H+) equivalent and no added oxidants. Preliminary mechanistic study supports this reaction manifold and shows the intersection of metal-catalyzed HAT and thiol radical trapping HAT catalytic cycles to be essential for effective catalysis. Together, this unique catalyst system allows us to reduce a variety of unactivated alkene substrates to their respective alkanes in high yields and diastereoselectivities and introduces a new approach to radical hydrogenation.
Boron trifluoride-catalyzed reaction of alkyl fluoride with silyl enolate, allylsilane, and hydrosilane
Hirano, Koji,Fujita, Kazuya,Yorimitsu, Hideki,Shinokubo, Hiroshi,Oshima, Koichiro
, p. 2555 - 2557 (2007/10/03)
Alkylation of silyl enolates with tert-alkyl or allylic fluorides proceeds smoothly in the presence of a catalytic amount of boron trifluoride to afford the corresponding carbonyl compounds. Allylation and reduction of alkyl fluorides with allylsilane and hydrosilane, respectively, occur under BF 3 catalysis.
