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

Sofia M. Bruno; Isabel S. Gonçalves; Martyn Pillinger; Carlos C. Romão; Anabela A. Valente

doi:10.1016/j.jorganchem.2017.12.001

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

Sofia M. Bruno, Isabel S. Gonçalves, Martyn Pillinger, Carlos C. Romão, Anabela A. Valente

Research output: Contribution to journal › Article

3 Citations (Scopus)

Abstract

The indenyl molybdenum carbonyl complexes [IndMo(CO) ₂ (L) _n ]BF ₄ (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 °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.

Original language	English
Pages (from-to)	12-17
Number of pages	6
Journal	Journal Of Organometallic Chemistry
Volume	855
DOIs	https://doi.org/10.1016/j.jorganchem.2017.12.001
Publication status	Published - 15 Jan 2018

Keywords

Acid catalysis
Epoxide alcoholysis
Indenyl ligand
Molybdenum carbonyl complexes

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10.1016/j.jorganchem.2017.12.001Licence: CC BY-NC-ND

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Bruno, S. M., Gonçalves, I. S., Pillinger, M., Romão, C. C., & Valente, A. A. (2018). Acid-catalyzed epoxide alcoholysis in the presence of indenyl molybdenum carbonyl complexes. Journal Of Organometallic Chemistry, 855, 12-17. https://doi.org/10.1016/j.jorganchem.2017.12.001

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title = "Acid-catalyzed epoxide alcoholysis in the presence of indenyl molybdenum carbonyl complexes",

abstract = "The indenyl molybdenum carbonyl complexes [IndMo(CO) 2 (L) n ]BF 4 (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 °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.",

keywords = "Acid catalysis, Epoxide alcoholysis, Indenyl ligand, Molybdenum carbonyl complexes",

author = "Bruno, {Sofia M.} and Gon{\cc}alves, {Isabel S.} and Martyn Pillinger and Rom{\~a}o, {Carlos C.} and Valente, {Anabela A.}",

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doi = "10.1016/j.jorganchem.2017.12.001",

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T1 - Acid-catalyzed epoxide alcoholysis in the presence of indenyl molybdenum carbonyl complexes

AU - Bruno, Sofia M.

AU - Gonçalves, Isabel S.

AU - Pillinger, Martyn

AU - Romão, Carlos C.

AU - Valente, Anabela A.

PY - 2018/1/15

Y1 - 2018/1/15

N2 - The indenyl molybdenum carbonyl complexes [IndMo(CO) 2 (L) n ]BF 4 (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 °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.

AB - The indenyl molybdenum carbonyl complexes [IndMo(CO) 2 (L) n ]BF 4 (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 °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.

KW - Acid catalysis

KW - Epoxide alcoholysis

KW - Indenyl ligand

KW - Molybdenum carbonyl complexes

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