1220698-87-2Relevant articles and documents
Somophilic alkynylation of unreactive alkenes enabled by iron-catalyzed hydrogen atom transfer
Ma, Mengtao,Shi, Zhuangzhi,Zhao, Binlin,Zhu, Tianxiang
, (2021/12/29)
We report an efficient and practical iron-catalyzed hydrogen atom transfer protocol for assembling acetylenic motifs into functional alkenes. Diversities of internal alkynes could be obtained from readily available alkenes and acetylenic sulfones with exc
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.
Iron-Catalyzed Coupling of Propargyl Bromides and Alkyl Grignard Reagents
Domingo-Legarda, Pablo,Soler-Yanes, Rita,Quirós-López, M. Teresa,Bu?uel, Elena,Cárdenas, Diego J.
, p. 4900 - 4904 (2018/09/10)
An iron-catalyzed Kumada-type cross-coupling reaction of propargyl halides with alkylmagnesium reagents is described. The reaction is fast, takes place in smooth conditions, tolerates several functional groups that would be able to react with the Grignard reagent, and may afford either allene or propargyl coupling derivatives. Factors involved in the observed regioselectivity have been studied.
Selective synthesis of allenes and alkynes through ligand-controlled, palladium-catalyzed decarboxylative hydrogenolysis of propargylic formates
Ohmiya, Hirohisa,Yang, Mingyu,Yamauchi, Yoshihiro,Ohtsuka, Yuhki,Sawamura, Masaya
scheme or table, p. 1796 - 1799 (2010/09/07)
Ligand-controlled regioselective palladium-catalyzed decarboxylative hydrogenolysis of propargylic formates is described. A wide range of allenes and alkynes were obtained by using either 1,2-diphenylphosphinoethane (DPPE) or 1,6-bisdiphenylphosphinohexane (DPPH) as a catalyst ligand.