Acid-catalyzed epoxide alcoholysis in the presence of indenyl molybdenum carbonyl complexes

abstract

The indenyl molybdenum carbonyl complexes [IndMo(CO)(2)(L)(n)]BF4 (L = NCMe with n = 3 (1), 2,2'-bipyridine (2) or 1,4,7-trimethyltriazacyclononane (3) with n = 1) promote epoxide alcoholysis under moderate reaction conditions. Complexes 1 and 2 showed the best performance for the alcoholysis of styrene oxide with different alcohol nucleophiles (acting as both reactant and solvent), leading to the corresponding 2-alkoxy-2-phenylethanol with 100% yield at 10 min and 35 degrees C. These catalytic results are far superior to those found for previously studied molybdenum carbonyl complexes. An efficient procedure for catalyst recovery and reuse without decrease in reaction rate is described. (C) 2017 Elsevier B.V. All rights reserved.

keywords

ORGANOMETALLIC LEWIS-ACIDS; RING SLIPPAGE; ROOM-TEMPERATURE; STYRENE EPOXIDE; MIXED-RING; EFFICIENT; ANALOGS

subject category

Chemistry

authors

Bruno, SM; Goncalves, IS; Pillinger, M; Romao, CC; Valente, AA

our authors

acknowledgements

This work was developed in the scope of the project CICECO - Aveiro Institute of Materials (POCI-01-0145-FEDER-007679) financed by national funds through the Fundacao para a Ciencia e a Tecnologia (FCT) (ref. UID/CTM/50011/2013) and Ministerio da Educacao e Ciencia (MEC) and when applicable, cofinanced by Fundo Europeu de Desenvolvimento Regional (FEDER) under the PT2020 Partnership Agreement. The FCT and the European Union are acknowledged for a post-doctoral grant to S. M. B. (SFRH/BPD/108845/2015), cofunded by Ministerio da Ciencia, Tecnologia e Ensino Superior (MCTES) and the European Social Fund through the program Programa Operacional Potencial Humano (POPH) of Quadro de Referencia Estrategica Nacional (QREN).

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