82944-29-4Relevant academic research and scientific papers
Thioether-Directed NiH-Catalyzed Remote γ-C(sp3)-H Hydroamidation of Alkenes by 1,4,2-Dioxazol-5-ones
Chen, Qishu,Du, Bingnan,Ouyang, Yuxin,Yu, Wing-Yiu
supporting information, p. 14962 - 14968 (2021/09/29)
A NiH-catalyzed thioether-directed cyclometalation strategy is developed to enable remote methylene C-H bond amidation of unactivated alkenes. Due to the preference for five-membered nickelacycle formation, the chain-walking isomerization initiated by the NiH insertion to an alkene can be terminated at the γ-methylene site remote from the alkene moiety. By employing 2,9-dibutyl-1,10-phenanthroline as the ligand and dioxazolones as the reagent, the amidation occurs at the γ-C(sp3)-H bonds to afford the amide products in up to 90% yield (>40 examples) with remarkable regioselectivity (up to 24:1 rr).
Heterocyclisation alkylante radicalaire par photolyse de sulfures ethyleniques. III. Photolyse de sulfures de butene-3 yle-1 et hexene-5 yle-1
Bastien, Gerard,Surzur, Jean-Marie
, p. 84 - 88 (2007/10/02)
Photolysis of allyl but-3-en-1-yl sulfide (I) gives the thiolan 3 and the 3-allylthiolan 4 resulting from "forbidden" 5-endotrig cyclization.Photolysis of allyl hex-5-en-1-yl sulfide (III) gives, besides the mixture of six- and seven-membered non-alkylated heterocycles 10 and 11, exclusively the alkylated 2-(but-3-enyl) thian 12.These and other results confirm and generalize the mechanism proposed earlier for the photolytic cyclization of pent-4-enyl sulfides.Photolitic cleavage of unsaturated allyl or benzyl sulfides gives the unsaturated thiyl radical.The unsaturated radical undergoes an intramolecular reversible addition out of the cage.Then the more stable cyclized radical is trapped selectively by the allyl or benzyl radical.
