Synthesis of α-Haloboronates by the Halogenation of gem-Diborylalkanes via Tetracoordinate Boron Species

Shangteng Liao; Jinchao Liang; Chaokun Li; Nan Chen; Kai Yang; Jinglong Chen; Qiuling Song

doi:10.1021/acs.orglett.3c00982

Synthesis of α-Haloboronates by the Halogenation of gem-Diborylalkanes via Tetracoordinate Boron Species

Org Lett. 2023 Apr 28;25(16):2928-2933. doi: 10.1021/acs.orglett.3c00982. Epub 2023 Apr 18.

Authors

Shangteng Liao¹, Jinchao Liang¹, Chaokun Li², Nan Chen², Kai Yang², Jinglong Chen¹, Qiuling Song^{2

3}

Affiliations

¹ College of Materials Science and Engineering, Fuzhou University, Fuzhou, Fujian Province 350108, China.
² Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian 350108, China.
³ School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.

PMID: 37071548
DOI: 10.1021/acs.orglett.3c00982

Abstract

α-Haloboronates have a wide range of applications in organic chemistry as synthetic synthons; however, traditional synthetic methods of α-haloboronates are harsh and complicated. Herein, we used ⁿBuLi as the nucleophilic reagent to attack the boron atom in gem-diborylalkanes to form tetracoordinate boron species and successfully achieved α-chloroboronates and α-bromoboronates with readily accessible electrophilic halogen reagents (NCS and NBS). The reaction is transition-metal-free and features a broad substrate scope and diversified valuable products.