Efficient synthesis of conjugated alkynyl cycloalkenones: Pd(PPh3)(4)-AgOAc-catalyzed direct coupling of 1-alkynes with 3-oxocycloalkenyl triflates

Palladium-silver acetate-catalyzed cross coupling of vinyl triflates and 1-alkynes was investigated. This strategy offered a very straightforward and efficient method for access to conjugated alkynyl cycloalkenones from the conjugated vinyl triflates and 1-alkynes. Moreover, the triflates derived fr...

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Published inApplied organometallic chemistry Vol. 24; no. 3; pp. 208 - 214
Main Authors Jiang, Chenggang, Zhang, Zonglei, Xu, Hangxian, Sun, Liang, Liu, Lanhai, Wang, Cunde
Format Journal Article
LanguageEnglish
Published MALDEN Wiley 01.03.2010
Subjects
Chemistry
Chemistry, Applied
Chemistry, Inorganic & Nuclear
Physical Sciences
Science & Technology
ANTITUMOR ANTIBIOTICS
STILLE TANDEM REACTION
conjugated alkynyl cycloalkenones
TERMINAL ACETYLENES
ONE-POT
palladium catalyst
Sonogashira-Linstrumelle reaction
silver acetate
BIOACTIVE ANALOGS
CHEMISTRY
ENEDIYNE
3-oxocycloalkenyl triflates
STEREOSELECTIVE-SYNTHESIS
SILVER SALTS
ENYNES
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Summary:Palladium-silver acetate-catalyzed cross coupling of vinyl triflates and 1-alkynes was investigated. This strategy offered a very straightforward and efficient method for access to conjugated alkynyl cycloalkenones from the conjugated vinyl triflates and 1-alkynes. Moreover, the triflates derived from 1,3-cycloalkadione needed no further purification and could be reacted immediately with 1-alkynes to provide the conjugated alkynyl cycloalkenanes in excellent overall yields. Copyright (C) 2009 John Wiley & Sons, Ltd.
ISSN:0268-2605
DOI:10.1002/aoc.1592