934667-85-3Relevant academic research and scientific papers
Switch in Selectivity for Formal Hydroalkylation of 1,3-Dienes and Enynes with Simple Hydrazones
Li, Chao-Jun,Lv, Leiyang,Qiu, Zihang,Yu, Lin
supporting information, p. 6466 - 6472 (2020/03/13)
Controlling reaction selectivity is a permanent pursuit for chemists. Regioselective catalysis, which exploits and/or overcomes innate steric and electronic bias to deliver diverse regio-enriched products from the same starting materials, represents a powerful tool for divergent synthesis. Recently, the 1,2-Markovnikov hydroalkylation of 1,3-dienes with simple hydrazones was reported to generate branched allylic compounds when a nickel catalyst was used. As part of the effort, shown here is that a complete switch of Markovnikov to anti-Markovnikov addition is obtained by changing to a ruthenium catalyst, thus providing direct and efficient access to homoallylic products exclusively. Isotopic substitution experiments indicate that no reversible hydro-metallation across the metal-π-allyl system occurred under ruthenium catalysis. Moreover, this protocol is applicable to the regiospecific hydroalkylation of the distal C=C bond of 1,3-enynes.
Ni-catalyzed Sonogashira coupling of nonactivated alkyl halides: Orthogonal functionalization of alkyl iodides, bromides, and chlorides
Vechorkin, Oleg,Barmaz, Delphine,Proust, Valerie,Hu, Xile
supporting information; experimental part, p. 12078 - 12079 (2010/01/15)
(Chemical Equation Presented) Ni-catalyzed Sonogashira coupling of nonactivated, β-H-containing alkyl halides, including chlorides, is reported. The coupling is tolerant to a wide range of functional groups, including ether, ester, amide, nitrile, keto, h
Hg(OAc)2·0.1Sc(OTf)3-catalyzed cycloisomerization of 2-(4-pentynyl)furan
Yamamoto, Hirofumi,Sasaki, Ikuo,Imagawa, Hiroshi,Nishizawa, Mugio
, p. 1399 - 1402 (2007/12/31)
Figure presented Although the Hg(OTf)2·3TMU-catalyzed Friedel-Crafts-type reaction of 3-(4-pentynyl)furan afforded the exo cyclization product, the reaction of 2-(4-pentynyl)furan furnished a very low yield. We found a 10:1 mixed reagent of Hg(
