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Electrophilic boron carboxylate and phosphinate complexes

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

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Abstract

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: 17 May 2019 13:05
URI: http://orca.cf.ac.uk/id/eprint/120919

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