7022-98-2Relevant articles and documents
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.
A new synthetic method for haloalkyl carboxylic esters from the radical ring cleavage of cyclic acetals with haloform
Hai-Xia, Lin,Liang-Heng, Xu,Nai-Ju, Huang
, p. 303 - 306 (2007/10/03)
A one-pot reaction of cyclic acetals with haloform catalyzed by AIBN(2,2'-azobisisobutyronitrile) provides a novel convenient way to prepare directly haloalkyl carboxylic esters in good yields.
REGIOSELECTIVE RING CLEAVAGE OF OXIRANES CATALYZED BY ORGANOTIN HALIDE - TRIPHENYLPHOSPHINE COMPLEX
Shibata, Ikuya,Baba, Akio,Matsuda, Haruo
, p. 3021 - 3024 (2007/10/02)
Vicinal chloroesters are formed in high yield from the reaction of oxiranes and benzoyl chloride in the presence of organotin halide - triphenylphosphine complex with enhanced regioselectivity in oxirane ring cleavage.