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Boronic, diboronic and boric acid esters of 1,8-naphthalenediol – synthesis, structure and formation of boronium salts

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Abstract

The 1,8-naphthalenediolate [1,8-O2C10H8] supported boronic and boric acid esters of general formula X-B(1,8-O2C10H8), where X = C6H5 (1a), C6F5 (2a), 3,4,5-F3-C6H2 (3a), 2,4,6-F3-C6H2 (4a), 2,6-F2-C6H3 (5a), 2,6-Cl2-C6H3 (6a), 2,4,6-Me3-C6H2 (7a), 2,6-(MeO)3-C6H3 (8a), Bun (9a), MeO (10a), OH (11a) and Cl (13a), were synthesized, NMR spectroscopically characterized, and the solid-state structures of 1a–5a, 8a and 10a determined by X-ray crystallography. The acceptor numbers of 1a–7a and 13a were determined and found to be similar to their catecholate analogues, R-Bcat, indicating similar Lewis acidities of these two classes of boronic acid esters. The reaction of B2(NMe2)4 with 1,8-naphthalenediol, followed by addition of HCl furnished the diboronic acid ester B2(1,8-O2C10H8)4 (16a) in ca. 70% yield. Cl-B(1,8-O2C10H8) (13a) was shown to react with O[double bond, length as m-dash]PEt3, DMAP, 1,10-phenanthroline and 2,2′-bipyridine, resp., to give the boronium salts [(Et3P[double bond, length as m-dash]O)2B(1,8-O2C10H8)]Cl (18a), [(DMAP)2B(1,8-O2C10H8)]Cl (22a), [(2,2′-bipyridine)B(1,8-O2C10H8)]Cl (23a) and [(1,10-phenanthroline)B(1,8-O2C10H8)]Cl (24a), which were characterized by NMR spectroscopy and X-ray crystallography.

Graphical abstract: Boronic, diboronic and boric acid esters of 1,8-naphthalenediol – synthesis, structure and formation of boronium salts

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Article information


Submitted
28 Feb 2020
Accepted
13 Mar 2020
First published
18 Mar 2020

Dalton Trans., 2020, Advance Article
Article type
Paper

Boronic, diboronic and boric acid esters of 1,8-naphthalenediol – synthesis, structure and formation of boronium salts

C. P. Manankandayalage, D. K. Unruh and C. Krempner, Dalton Trans., 2020, Advance Article , DOI: 10.1039/D0DT00745E

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