Cardiff University | Prifysgol Caerdydd ORCA
Online Research @ Cardiff 
WelshClear Cookie - decide language by browser settings

Electrophilic boron carboxylate and phosphinate complexes

Zhu, Diya, LaFortune, James H. W., Melen, Rebecca L. ORCID: and Stephan, Douglas W. 2019. Electrophilic boron carboxylate and phosphinate complexes. Dalton Transactions 48 (6) , pp. 2038-2045. 10.1039/C8DT04818E

[thumbnail of c8dt04818e.pdf]
PDF - Published Version
Available under License Creative Commons Attribution.

Download (1MB) | Preview
License URL:
License Start date: 9 January 2019


The reactions of a series of carboxylic acids with H2B(C6F5)·SMe2 are shown to afford species of the form [RC(O)OB(C6F5)]2O, (R = Tol 1, Ph 2, C6F53, Me2BrC 4, Me 5) in 87–95% yields with the concurrent reduction of the carboxylic acid to the corresponding aldehyde. A mechanism for the formation of 1–5 is proposed to proceed via a cyclic eight-membered ring species. Analogues of these species were prepared via reactions of carboxylic and phosphinic acids with HB(C6F5)2 and H2B(C6F5)·SMe2, respectively, to give [TolC(O)OB(C6F5)2]26, [(C6F5)C(O)OB(C6F5)2]27, and [Ph2P(O)OBH(C6F5)]28. These products react subsequently to give TolC(O)OBH(C6F5)(NC5H4NMe2) 9 and Ph2P(O)OBH(C6F5)(NC5H4NMe2) 10. The acyloxyborate derivatives 1–4 were shown to be inactive in mediating the direct amidation of carboxylic acids, consistent with previous observations that infer the need for a sterically congested environment about the boron centres.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1477-9226
Funders: EPSRC
Date of First Compliant Deposit: 19 March 2019
Date of Acceptance: 8 January 2019
Last Modified: 25 Oct 2022 13:51

Citation Data

Cited 1 time in Scopus. View in Scopus. Powered By Scopus® Data

Actions (repository staff only)

Edit Item Edit Item


Downloads per month over past year

View more statistics