Pd-Catalyzed B–H Aryl/Alkenylation of 1,2-Azaborines

Direct functionalization of 1,2-azaborines to construct B–C bonds remains challenging. Here, we report a Pd-catalyzed B–H aryl/alkenylation reaction of 1,2-azaborines. The method provides a general platform to access diverse boron-substituted 1,2-azaborine compounds (>60 examples). The synthetic utility is highlighted through the late-stage modification of bioactive molecules, as well as the preparation and transformations of the 10B-enriched 1,2-azaborine product and the synthesis of four BN isostere analogues of bioactive molecules. And the reaction mechanism is also explored and discussed.

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Publication Details

Journal
ACS Catalysis
Published
2024-11-04
DOI
https://doi.org/10.1021/acscatal.4c04576
Citations
4
Primary Topic
Organoboron and organosilicon chemistry
Type
article
Field-Weighted Citation Impact
1.00

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article

Pd-Catalyzed B–H Aryl/Alkenylation of 1,2-Azaborines

P. P. Su, Peiyuan Yu, Kai Huai Yang, Qiuling Song et al.
4 citations
ACS Catalysis
Organoboron and organosilicon chemistry
1.00
article

Pd-Catalyzed B–H Aryl/Alkenylation of 1,2-Azaborines

P. P. Su, Peiyuan Yu, Kai Huai Yang, Qiuling Song, Zhen Zhang, Dandan Jiang
article en
4 citations

Abstract

Direct functionalization of 1,2-azaborines to construct B–C bonds remains challenging. Here, we report a Pd-catalyzed B–H aryl/alkenylation reaction of 1,2-azaborines. The method provides a general platform to access diverse boron-substituted 1,2-azaborine compounds (>60 examples). The synthetic utility is highlighted through the late-stage modification of bioactive molecules, as well as the preparation and transformations of the 10B-enriched 1,2-azaborine product and the synthesis of four BN isostere analogues of bioactive molecules. And the reaction mechanism is also explored and discussed.

ACS CatalysisVol. 14(22)
Southern University of Science and Technology (CN), Henan Normal University (CN), Fuzhou University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Fujian Province, National Key Research and Development Program of China, Science and Technology Planning Project of Shenzhen Municipality
Openalex Percentile: Top 26%
Organoboron and organosilicon chemistry
1.00
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Pd-Catalyzed B–H Aryl/Alkenylation of 1,2-Azaborines — P. P. Su, Peiyuan Yu, et al. · ACS Catalysis (2024) | TGRS Research Map | TGRS