Electrochemical deconstruction of alkyl substituted boron clusters to produce alkyl boronate esters

Huanhuan Xie; Xinying Gao; Beibei Dong; Haoyang Wang; Alexander M Spokoyny; Xin Mu

doi:10.1039/d4cc04232h

Electrochemical deconstruction of alkyl substituted boron clusters to produce alkyl boronate esters

Chem Commun (Camb). 2024 Sep 23. doi: 10.1039/d4cc04232h. Online ahead of print.

Authors

Huanhuan Xie¹, Xinying Gao¹, Beibei Dong¹, Haoyang Wang², Alexander M Spokoyny^{3

4}, Xin Mu¹

Affiliations

¹ Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, 200237, Shanghai, China. xinmu@ecust.edu.cn.
² Laboratory of Mass Spectrometry Analysis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China. haoyangwang@sioc.ac.cn.
³ Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095, USA. spokoyny@chem.ucla.edu.
⁴ California NanoSystems Institute (CNSI), University of California, Los Angeles, Los Angeles, California 90095, USA.

PMID: 39311548
DOI: 10.1039/d4cc04232h

Abstract

Closo-Hexaborate (closo-B₆H₆^2-) can engage in nucleophilic substitution reactions with a wide variety of alkyl electrophiles. The resulting functionalized boron clusters undergo oxidative electrochemical deconstruction, selectively cleaving B-B bonds while preserving B-C bonds in these species. This approach allows the conversion of multinuclear boron clusters into single boron site organoboranes. Trapped boron-based fragments were isolated from the electrochemical cluster deconstruction process, providing further mechanistic insights into the developed reaction.