Abstract
Inspired by the demand of green and sustainable chemistry, modern synthetic chemists have devoted to develop general and practical methods to construct complex molecules. Due to the sp hybridization of the triple bond and the connected halogen atom, haloalkynes, such as bromoalkynes, chloroalkynes and iodoalkynes, have shown both controllable electrophilic and nucleophilic properties, rendering them highly versatile and robust synthons. As the immense usefulness of haloalkynes, impressive efforts have been devoted to this area in the past decades and many novel chemical reactions have been developed. In this chapter, we will introduce the physical property of haloalkynes, classify the reaction intermediate types derived from haloalkynes, and also hope to give the readers a comprehensive understanding of haloalkyne chemistry.
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References
Li C, Trost BM (2008) Green chemistry for chemical synthesis. Proc Natl Acad Sci 105:13197–13202
Wu W, Jiang H (2014) Haloalkynes: a powerful and versatile building block in organic synthesis. Acc Chem Res 47:2483–2504
Laurence C, Queignec-Cabanetos M, Dziembowska T, Queignec R, Wojtkowiak B (1981) 1-Iodoacetylenes. 1. Spectroscopic evidence of their complexes with Lewis bases. A spectroscopic scale of soft basicity. J Am Chem Soc 103:2567–2573
Gao K, Goroff NS (2000) Two new iodine-capped carbon rods. J Am Chem Soc 122:9320–9321
Rege PD, Malkina OL, Goroff NS (2001) The effect of Lewis bases on the 13C NMR of Iodoalkynes. J Am Chem Soc 124:370–371
Ott E, Dittus G (1943) Polymerisation und Reaktionen mit Ammoniak, Aminen, Alkoholaten und Natriummalonester. Chem Ber 76:80–84
Poulsen TB, Barnardi L, Aleman J, Overgaard J, Jørgensen KA (2007) Organocatalytic asymmetric direct α-alkynylation of cyclic β-ketoesters. J Am Chem Soc 129:441–449
Boger DL, Brunette SR, Garbaccio RM, Boger DL, Brunette SR, Garbaccio RM (2001) Synthesis and evaluation of a series of C3-substituted CBI analogues of CC-1065 and the Duocarmycins. J Org Chem 66:5163–5173
Trofimov A, Chernyak N, Gevorgyan V (2008) Dual role of Alkynyl halides in one-step synthesis of Alkynyl epoxides. J Am Chem Soc 130:13538–13539
Brand JP, Waser J (2012) Electrophilic alkynylation: the dark side of acetylene chemistry. Chem Soc Rev 41:4165–4179
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Jiang, H., Zhu, C., Wu, W. (2016). Introduction. In: Haloalkyne Chemistry. SpringerBriefs in Molecular Science(). Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-49001-3_1
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DOI: https://doi.org/10.1007/978-3-662-49001-3_1
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