Sonogashira Reaction of Aryl and Heteroaryl Halides with Terminal Alkynes Catalyzed by a Highly Efficient and Recyclable Nanosized MCM-41 Anchored Palladium Bipyridyl Complex 英文参考文献.docVIP

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Sonogashira Reaction of Aryl and Heteroaryl Halides with Terminal Alkynes Catalyzed by a Highly Efficient and Recyclable Nanosized MCM-41 Anchored Palladium Bipyridyl Complex 英文参考文献.doc

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Sonogashira Reaction of Aryl and Heteroaryl Halides with Terminal Alkynes Catalyzed by a Highly Efficient and Recyclable Nanosized MCM-41 Anchored Palladium Bipyridyl Complex 英文参考文献

Molecules 2010, 15, 9157-9173; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Sonogashira Reaction of Aryl and Heteroaryl Halides with Terminal Alkynes Catalyzed by a Highly Efficient and Recyclable Nanosized MCM-41 Anchored Palladium Bipyridyl Complex Bo-Nan Lin 1, Shao-Hsien Huang 1, Wei-Yi Wu 1, Chung-Yuan Mou 2 and Fu-Yu Tsai 1,* 1 Institute of Organic and Polymeric Materials, National Taipei University of Technology, Taipei 106, Taiwan 2 Department of Chemistry, National Taiwan University, Taipei 106, Taiwan * Author to whom correspondence should be addressed; E-Mail: fuyutsai@.tw; Fax: +886-2-2731-7174. Received: 11 November 2010; in revised form: 6 December 2010 / Accepted: 9 December 2010 / Published: 10 December 2010 Abstract: A heterogeneous catalyst, nanosized MCM-41-Pd, was used to catalyze the Sonogashira coupling of aryl and heteroaryl halides with terminal alkynes in the presence of CuI and triphenylphosphine. The coupling products were obtained in high yields using low Pd loadings to 0.01 mol%, and the nanosized MCM-41-Pd catalyst was recovered by centrifugation of the reaction solution and re-used in further runs without significant loss of reactivity. Keywords: Sonogashira reaction; mesoporous silica; palladium complex; recyclable catalyst; heterogeneous catalysis 1. Introduction The reaction of aryl halides or vinyl halides with terminal alkynes catalyzed by a Pd(II)/Cu(I) system is known as the Sonogashira coupling, and is one of the most powerful methods for the straightforward construction of sp2–sp carbon–carbon bonds in synthetic chemistry [1–7]. This methodology has been widely applied to prepare biologically-active molecules [8–13], natural Molecules 2010, 15 9158 products [14–17], conducting polymers/engineering materials [18,19], and macrocycles with acetylene links [20,21]. The Sonoga