12 May 2014 (online)
Dedicated to Professor Dr. Grzegorz Mlostoń, Dr. Emilia Obijalska, and my family.
Phenylacetylene (1-phenylethyne, 1-phenylacetylene) is a terminal alkyne which under standard conditions is a light yellow liquid with a characteristic odor. It can be conveniently prepared via the reaction of benzaldehyde with the Bestmann–Ohira reagent in the presence of a base at room temperature.[1a] Other methods applied for its preparation consists in the treatment of acetophenone with lithium diisopropylamide (LDA) and diethyl chlorophosphate.[1b] Phenylacetylene is widely applied as a versatile building block, for example in Kinugasa reactions, Diels–Alder reactions, 1,3-dipolar cycloaddition reactions, diverse transition-metal-supported coupling reactions, and in nucleophilic additions.
- 1a Möller S, Liepold B, Bestmann HJ. Synlett 1996; 521
- 1b Negishi E, King AO, Klima WL. J. Org. Chem. 1980; 40: 2526
- 2 Saito T, Kikuchi T, Tanabe H, Yahiro J, Otani T. Tetrahedron Lett. 2009; 50: 4969
- 3 Chen J.-H, Liao S.-H, Sun X.-L, Shen Q, Tang Y. Tetrahedron 2012; 68: 5042
- 4 Grzeszczyk B, Poławska K, Shaker S, Stecko Y, Mames MA, Woźnicka M, Chmielewski M, Furman B. Tetrahedron 2012; 68: 10633
- 5 Ji D.-M, Xu M.-H. Tetrahedron Lett. 2009; 50: 2952
- 6 Namitharan K, Pitchumani K. Eur. J. Org. Chem. 2010; 411
- 7 Brotherton WS, Clark RJ, Zhu L. J. Org. Chem. 2012; 77: 6443
- 8 Liu J, Zhang N, Yue Y, Wang D, Zhang Y, Zhang X, Zhuo K. RSC Adv. 2013; 3: 3865
- 9 Hellal M, Cuny GD. Tetrahedron Lett. 2011; 52: 5508
- 10 Chouhan M, Senwar KR, Kumar K, Sharma R, Nair VA. Synthesis 2014; 46: 195
- 11 Patil NT, Raut VS, Tella RB. Chem. Commun. 2013; 49: 570