Chloro(η2,η2-Cycloocta-1,5-Diene){1-[(2-[(S)-1-(Hydroxymethyl)-3-Methylbutyl]Amino)-2-Oxoethyl]-3-(1-Naphthalenylmethyl)Benzimidazol-2-Ylidene}Rhodium(I)

Abstract

Commercially available and air- and moisture-stable rhodium complex [Rh(OH)(cod)]2 (2) was utilized in the synthesis of [RhX(cod)(NHC)] (3). The presence of an OH group in complex 2 serves as an internal base, facilitating the deprotonation of the C–H bond of the azolium ring in the hydroxyamide-substituted benzimidazolium salt 1. This reaction between 1 and 2 proceeded in THF at room temperature without temperature control, affording the desired NHC/Rh complex 3 in excellent yield. The characterization of complex 3 was accomplished through NMR and HRMS analyses, revealing its existence as a diastereomeric mixture of two NHC/Rh complexes. Furthermore, its catalytic performance was briefly evaluated in the reaction between 2-naphthaldehyde (5) and phenylboronic acid (6).