7217-47-2Relevant articles and documents
Dehalogenative Deuteration of Unactivated Alkyl Halides Using D2O as the Deuterium Source
Xia, Aiyou,Xie, Xin,Hu, Xiaoping,Xu, Wei,Liu, Yuanhong
, p. 13841 - 13857 (2019)
The general dehalogenation of alkyl halides with zinc using D2O or H2O as a deuterium or hydrogen donor has been developed. The method provides an efficient and economic protocol for deuterium-labeled derivatives with a wide substrate scope under mild reaction conditions. Mechanistic studies indicated that a radical process is involved for the formation of organozinc intermediates. The facile hydrolysis of the organozinc intermediates provides the driving force for this transformation.
Diastereoselective tandem addition-cyclization reactions of unsaturated tertiary amines initiated by photochemical electron transfer (PET)
Bertrand,Hoffmann,Humbel,Pete
, p. 8690 - 8703 (2007/10/03)
Polycyclic molecules and tetrahydroquinoleines were obtained in a tandem reaction involving the diastereoselective addition of α-aminoalkyl radicals to (5R)-5-menthyloxy-2[5H]-furanone 1. The facial diastereoselectivity on 1 is ≥90%. The α-aminoalkyl radicals were produced from tertiary amines by photochemical-induced electron transfer. When N, N-dialkylanilines 19 were used as starting tertiary amines, a rearomatization step was involved and important side reactions of 1 were observed. A mechanistic study involving isotopic labeling of the starting amine indicated that the byproducts resulted from reduction of I during the rearomatization process. An efficient optimization of the reaction was obtained by simply adding acetone or cyclopentanone as mild oxidants to the reaction mixture. The side products resulting from reduction of the furanone 1 were completely suppressed under these conditions, and the yields of the tetrahydroquinolines 21ai, 22a-f, and 26g-i were doubled.