110211-33-1Relevant academic research and scientific papers
Oxidative Dimerization of Silylallenes via Activation of the Allenic C(sp2)-H Bond Catalyzed by Copper(I) Chloride and N-Hydroxyphthalimide
Sabbasani, Venkata R.,Lee, Daesung
, p. 4878 - 4881 (2015)
Novel oxidative dimerization of silylallenes is described. Treatment of silylallenes with a catalytic amount of copper(I) chloride, a substoichiometric amount of N-hydroxyphthalamide, and a stoichiometric amount of a terminal oxidant diacetoxyiodobenzene
Facile Alder-Ene Reactions of Silylallenes Involving an Allenic C(sp2)-H Bond
Sabbasani, Venkata R.,Huang, Genping,Xia, Yuanzhi,Lee, Daesung
supporting information, p. 17210 - 17214 (2016/01/25)
Facile and selective Alder-ene reactions of silylallenes involving the activation of an allenic C(sp2)-H over an allylic C(sp3)-H bond is described. In this ene reaction, the presence of a silyl substituent was found to be critical for the observed reactivity and selectivity since the corresponding alkyl-substituted allenes show different reaction profiles. Computational studies show that the origin of this unusual reactivity is the lower bond dissociation energy of the α-C(sp2)-H bond in silylallenes compared to the corresponding nonsilylated allenes.
Selectivity control in alkylidene carbene-mediated C-H insertion and allene formation
Zheng, Jun-Cheng,Yun, Sang Young,Sun, Chunrui,Lee, Nam-Kyu,Lee, Daesung
experimental part, p. 1086 - 1099 (2011/04/16)
Regioselectivity of alkylidene carbene-mediated C-H insertion was explored utilizing electronic, conformational, steric, and stereoelectronic effects. Relying on these factors, highly regio-and chemoselective carbene insertion reaction of C-H bonds in different environments could be obtained. The observed selectivity clearly indicates that an electronic effect plays a more important role than steric effect. In general, C-H bonds in conformationally rigid cyclic environments are less reactive than those in acyclic systems toward carbene insertion, and in this situation, a competing intermolecular reaction between alkylidene carbene and trimethylsilyldiazomethane led to the formation of allenylsilanes. The formation of allenylsilane becomes more favorable as the concentration of reaction becomes higher, as well as the C-H bonds undergoing insertion becomes electronically and conformationally deactivated.
PALLADIUM-CATALYZED REDUCTION OF PROPARGYLIC ACETATES WITH SmI2. A MILD AND CONVENIENT METHOD FOR THE PREPARATION OF ALLENES
Tabuchi, Takanori,Inanaga, Junji,Yamaguchi, Masaru
, p. 5237 - 5240 (2007/10/02)
A highly regioselective reduction of propargylic acetates has been attained by using SmI2 and catalytic Pd(0) in the presence of 2,4-dimethyl-3-pentanol affording various types of allenes in high yields.
