Tetrahedron letters2022,Vol.918.DOI:10.1016/j.tetlet.2022.153645

Organoborane-catalyzed selective 1,2-reduction of alkynones with hydride transfer: Synthesis of benzyl alkynes

Zhai, Lele Yang, Zhigang Man, Qinghong Yang, Mingyu Ren, Yangqing Wang, Lei Li, Huilin She, Xuegong
Tetrahedron letters2022,Vol.918.DOI:10.1016/j.tetlet.2022.153645

Organoborane-catalyzed selective 1,2-reduction of alkynones with hydride transfer: Synthesis of benzyl alkynes

Zhai, Lele 1Yang, Zhigang 1Man, Qinghong 1Yang, Mingyu 1Ren, Yangqing 1Wang, Lei 1Li, Huilin 1She, Xuegong1
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作者信息

  • 1. Lanzhou Univ
  • 折叠

Abstract

Benzyl alkynes are important organic building blocks in organic synthesis. We report herein a B(C6F5)(3)-catalyzed site-selective 1,2-reduction of readily available alkynones to access benzyl alkyne derivatives. Under the developed conditions, an array of alkynone substrates are transformed into the corresponding benzyl alkyne products in good to excellent yields. This transformation displays many advantages including transition metal-free, mild reaction conditions, low catalyst loading (5 mol%), high yield (up to 99%), broad substrate scope and functional group tolerance. Moreover, the method's utility is demonstrated by the diverse transformation of the benzyl alkyne products into other useful chemical compounds in only one-step operation. This protocol offers an expedient way to the synthesis of benzyl alkynes. (C) 2022 Elsevier Ltd. All rights reserved.

Key words

B(C6F5)(3)/Alkynone/Benzyl alkyne/Organoborane catalysis/Lewis acid/CROSS-COUPLING REACTION/TERMINAL ALKYNES/ISOMERIZATION/DERIVATIVES/ACTIVATION

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出版年

2022
Tetrahedron letters

Tetrahedron letters

CCR
ISSN:0040-4039
参考文献量40
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