141191-82-4Relevant articles and documents
Copper-Catalyzed Regioselective and Stereoselective Coupling of Grignard Reagents with Pent-1-en-4-yn-3-yl Benzoates: A Shortcut to (Z) -1,5-Disubstituted Pent-3-en-1-ynes from Accessible Starting Materials
Chen, Fenglin,Chen, Yanjiao,Cao, Hongen,Xu, Qing,Yu, Lei
, p. 14158 - 14164 (2018/11/30)
Copper-catalyzed coupling of Grignard reagents with pent-1-en-4-yn-3-yl benzoates occurs regioselectively at the terminal alkenyl carbon rather than the alkynyl site, leading to the stereoselective formation of unexpected (Z)-1,5-disubstituted pent-3-en-1-ynes without generation of the initially expected alkenyl allene products. By using easily accessible starting materials, this reaction can provide direct access to thermodynamically unfavorable Z-configured enynes, which widely exist in many bioactive natural products, such as the anti-inflammatory components in henna.
Cu-catalyzed Fe-driven Csp-Csp and C sp-Csp2 cross-coupling: An access to 1,3-diynes and 1,3-enynes
Ahammed, Sabir,Kundu, Debasish,Ranu, Brindaban C.
, p. 7391 - 7398 (2014/09/17)
An efficient Csp-Csp cross-coupling of alkynyl bromide and pinacol ester of alkynyl boronic acid catalyzed by CuFe 2O4 nanoparticles has been accomplished in dimethyl carbonate to produce unsymmetric 1,3-diynes. This protocol is also extended for the Csp-Csp2 coupling of alkynyl bromide and alkenyl boronic acid to provide conjugated 1,3-enynes. The aliphatic, aromatic, and heteroaromatic alkynes couple with various substituted alkynyl/alkenyl boronates/boronic acids by this procedure to furnish a library of 1,3-diynes and enynes in high yields. The catalyst was easily separated by an external magnet and recycled 10 times.
Skeletal change in the PNP pincer ligand leads to a highly regioselective alkyne dimerization catalyst
Weng, Wei,Guo, Chengyun,Celenligil-Cetin, Remle,Foxman, Bruce M.,Ozerov, Oleg V.
, p. 197 - 199 (2008/02/07)
A Rh complex of a bulky diarylamino-based PNP pincer ligand is a robust catalyst for the dimerization of terminal alkynes and highly selective for the trans-enyne product. The Royal Society of Chemistry 2006.