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Catalysts 2017, 7(7), 195; doi:10.3390/catal7070195

Intramolecular Transfer of Pd Catalyst on Carbon–Carbon Triple Bond and Nitrogen–Nitrogen Double Bond in Suzuki–Miyaura Coupling Reaction

Department of Materials and Life Chemistry, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan
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Academic Editor: Ioannis D. Kostas
Received: 24 March 2017 / Revised: 19 June 2017 / Accepted: 20 June 2017 / Published: 23 June 2017
(This article belongs to the Special Issue Suzuki–Miyaura Cross-Coupling Reaction and Potential Applications)
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Abstract

Intramolecular transfer of t-Bu3P-ligated Pd catalyst on a carbon–carbon triple bond (C≡C) and nitrogen–nitrogen double bond (N=N) was investigated and compared with the case of a carbon–carbon double bond (C=C), which is resistant to intramolecular transfer of the Pd catalyst. Suzuki–Miyaura coupling reaction of equimolar 4,4’-dibromotolan (1a) or 4,4’-dibromoazobenzene (1b) with 3-isobutoxyphenylboronic acid (2) was carried out in the presence of t-Bu3P-ligated Pd precatalyst 3 and KOH/18-crown-6 as a base at room temperature. In both cases, the diphenyl-substituted product was selectively obtained, indicating that the Pd catalyst walked from one benzene ring to the other through the C≡C or N=N bond after the first substitution with 2. Taking advantage of this finding, we conducted unstoichiometric Suzuki–Miyaura polycondensation of 1.3 equiv. of 1 and 1.0 equiv. of phenylenediboronic acid (ester) 6 in the presence of 3 and CsF/18-crown-6 as a base, obtaining high-molecular-weight conjugated polymer with a boronic acid (ester) moiety at both ends, contrary to the Flory principle. View Full-Text
Keywords: palladium catalyst; Suzuki coupling; catalyst transfer; conjugated polymer; unstoichometric polycondensation palladium catalyst; Suzuki coupling; catalyst transfer; conjugated polymer; unstoichometric polycondensation
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MDPI and ACS Style

Kamigawara, T.; Sugita, H.; Mikami, K.; Ohta, Y.; Yokozawa, T. Intramolecular Transfer of Pd Catalyst on Carbon–Carbon Triple Bond and Nitrogen–Nitrogen Double Bond in Suzuki–Miyaura Coupling Reaction. Catalysts 2017, 7, 195.

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