127915-64-4Relevant academic research and scientific papers
Sequential O-H/C-H bond insertion of phenols initiated by the gold(I)-catalyzed cyclization of 1-bromo-1,5-enynes
Speck, Klaus,Karaghiosoff, Konstantin,Magauer, Thomas
supporting information, p. 1982 - 1985 (2015/04/27)
The development of a sequential O-H/C-H bond functionalization of phenols initiated by the cationic gold(I)-catalyzed cyclization of 1-bromo-1,5-enynes to produce (2-bromocyclopent-2-en-1-yl)phenols is reported. This unprecedented domino transformation efficiently proceeds under mild conditions (5 mol % of (t-Bu)3PAuNTf2, CH2Cl2, 0-23 °C) via an intermediate aryl alkyl ether which collapses at ambient temperature to undergo a 1,2-hydride shift followed by C-H insertion of the phenol.
Synthesis of Allenes by 1,6-Addition of Organocuprates to Polarized Enynes
Krause, Norbert
, p. 2173 - 2180 (2007/10/02)
Ten β-allenic esters, ketones, and thioesters 15 bearing alkyl, alkenyl, aryl, and trimethylsilyl groups are synthesized in 57-85percent yield by 1,6-addition of organocuprates to polarized enynes 10.The dependence of the regioselectivity of the protonation of the allenyl enolate intermediate 7 on the protonating agent is studied; pure allenes are obtained by quenching the intermediate with pivalic acid at -80 deg C.The method is applied in a short synthesis of pseudoionone (18).
