端炔的硼化-迁移加成-氧化和硼化-氧化

doi:10.3866/PKU.DXHX202005028

Abstract

Abstract:

The hydroboration-oxidation of 1-alkynes is important in fundamental organic chemistry. As an extension, this paper introduces the boration-migratory addtion-oxidation and boration-oxidation of 1-alkynes, which are closely related to yet more advanced than the knowledge of fundamental organic chemistry. The former one reaction converts 1-alkynes to aldehydes, while the latter two to ketones, caroboxylic acids, esters, and amides. Teaching these three types of reactions is helpful to improve the students' knowledge reserves and cognitive ability.

Key words: 1-Alkyne, Hydroboration, Boration, Migratory addition, Oxidation

Zhanhui Yang, Yang Chen. The Boration-Migratory Addtion-Oxidation and Boration-Oxidation of 1-Alkynes[J].University Chemistry, 2021, 36(4): 2005028.

Figures/Tables 4

References 12

1	邢其毅; 裴伟伟; 徐瑞秋; 裴坚. 基础有机化学, 第4版北京: 北京大学出版社, 2016.
2	Vollhardt P. K. ; Schore N. Organic Chemistry 8th ed New York, USA: W. H. Freeman and Company, 2018.
3	Negishi E. ; Idacavage M. J. Org. React. 1985, 33, 1.
4	Brown H. C. ; Levy A. B. ; Milland M. M. J. Am. Chem. Soc. 1975, 97, 5017. doi: 10.1021/ja00850a047
5	Pelter A. ; Harrison C. R. ; Kirkpatrick D. Chem. Commun. 1973, 544.
6	Pelter A. ; Harrison C. R. ; Kirkpatrick D. Tetrahedron Lett. 1973, 14, 4491.
7	Pelter A. ; Gould K. J. ; Harrison; C. R. Tetrahedron Lett. 1975, 16, 3327. doi: 10.1016/S0040-4039(00)91440-0
8	Naruse M. ; Utimoto K. ; Nozaki H. Tetrahedron 1974, 30, 3037. doi: 10.1016/S0040-4020(01)97550-7
9	Baker M. A. ; Demoret R. M. ; Ohtawa M. ; Shenvi R. A. Nature 2019, 575, 643. doi: 10.1038/s41586-019-1690-5
10	Li C. ; Zhao P. ; Li R. ; Zhang B. ; Zhao W. Angew. Chem. Int. Ed. 2020, 59, 10913. doi: 10.1002/anie.202000988
11	Jiang Y. ; Diagne A. B. ; Thomson R. J. ; Schaus S. E. J. Am. Chem. Soc. 2017, 139, 1998. doi: 10.1021/jacs.6b11937
12	Elkin P. K. ; Levin V. V. ; Dilman A. D. ; Struchkova M. I. ; Belyakov P. A. ; Arkhipov D. E. ; Korlyukov A. A. ; Tartakovsky V. A. Tetrahedron Lett. 2011, 52, 5259. doi: 10.1016/j.tetlet.2011.07.141

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The Boration-Migratory Addtion-Oxidation and Boration-Oxidation of 1-Alkynes

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