Divergent synthesis of 5- and 4-(2,1-azaborine) substituted isoxazoles via regioselective [3 + 2] cycloadditions of nitrile oxides and B-ethynyl-1,2-azaborines - Details

author：

He, Yong (He, Yong.) ^[1] | Wang, Hao (Wang, Hao.) ^[2] | Zhou, Yao (Zhou, Yao.) ^[3] | Yang, Kai (Yang, Kai.) ^[4] | Song, Qiuling (Song, Qiuling.) ^[5]

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Abstract：

Herein　we　report　the　highly　regioselective　synthesis　of　5-　and　4-(2,1-azaborine)　substituted　isoxazoles　via　[3　+　2]　cycloaddition　reactions　between　nitrile　oxides　and　B-ethynyl-1,2-azaborines.　5-(2,1-Azaborine)　substituted　isoxazoles　are　favored　in　the　absence　of　a　catalyst,　while　4-(2,1-azaborine)　substituted　isoxazoles　are　favored　in　the　presence　of　a　ruthenium　catalyst.　The　reaction　exhibits　excellent　regioselectivity,　mild　reaction　conditions,　high　functional　group　tolerance　and　a　broad　substrate　scope.　©　2023　The　Royal　Society　of　Chemistry.

Keyword：

Catalysts Cycloaddition Nitrogen oxides Regioselectivity

Community：

[ 1 ] [He, Yong]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, Fuzhou University, Fujian, Fuzhou; 350108, China
[ 2 ] [Wang, Hao]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, Fuzhou University, Fujian, Fuzhou; 350108, China
[ 3 ] [Zhou, Yao]Hubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi; 435002, China
[ 4 ] [Yang, Kai]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, Fuzhou University, Fujian, Fuzhou; 350108, China
[ 5 ] [Song, Qiuling]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, Fuzhou University, Fujian, Fuzhou; 350108, China
[ 6 ] [Song, Qiuling]Institute of Next Generation Matter Transformation, College of Materials Science Engineering, Huaqiao University, 668 Jimei Boulevard, Fujian, Xiamen; 361021, China
[ 7 ] [Song, Qiuling]School of Chemistry and Chemical Engineering, Henan Normal University, Henan, Xinxiang; 453007, China

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Source ：

Organic Chemistry Frontiers

ISSN： 2052-4110

Year： 2022

Issue： 1

Volume： 10

Page： 127-132

5 . 4

JCR@2022

4 . 6 0 0

JCR@2023

ESI HC Threshold：74

JCR Journal Grade：1

CAS Journal Grade：1

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SCOPUS Cited Count：

ESI Highly Cited Papers on the List： 0 Unfold All

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Chinese Cited Count：

30 Days PV： 2

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