Highly regioselective hydroselenation and double-bond isomerization of terminal alkynes with benzeneselenol catalyzed by bis(triphenylphosphine) palladium(II) dichloride

Journal of Organometallic Chemistry

Volumn 696, Issue 1, 2011, Pages 450-455

  Ozaki, Toshiya ^a   Kotani, Mao ^a   Kusano, Hiroki ^a   Nomoto, Akihiro ^a   Ogawa, Akiya ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

Double bond isomerization; Markovnikov addition; Palladium; Selenol; Vinyl selenide

Indexed keywords

ALKENYL; BENZENESELENOL; DOUBLE-BOND ISOMERIZATION; GOOD YIELD; HYDROSELENATION; MARKOVNIKOV ADDITION; REGIO-SELECTIVE; REGIOSELECTIVE ADDITION; SELENIDES; SELENOL; TERMINAL ALKYNE; TRIPHENYL PHOSPHINES;

ACETYLENE; CATALYSIS; ISOMERIZATION; ORGANOMETALLICS; PALLADIUM; PALLADIUM COMPOUNDS; REGIOSELECTIVITY; SELENIUM COMPOUNDS;

ISOMERS;

EID: 78649888068     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2010.10.005     Document Type: Article

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46. 3 (2 mol%) in benzene at 80 °C for 16 h, the double bond isomerization proceeded to give 9 % of 4a [E/Z = 78/22] with the recovery of 2a (65%). The addition of selenol (2 mol%) to this reaction system accelerated the double bond isomerization (17% of 4a [E/Z = 71/29] and 47% of 2a were obtained).
47. 6 (0.5 mL) at 80 °C for 16 h, but the E/Z ratio was not changed at all [E/Z = 14/86].