Photogeneration of a phosphonium alkylidene olefin metathesis catalyst

Andrey Y. Khalimon; Erin M. Leitao; Warren E. Piers

doi:10.1021/om3005965

Photogeneration of a phosphonium alkylidene olefin metathesis catalyst

Andrey Y. Khalimon, Erin M. Leitao, Warren E. Piers

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

Treatment of ruthenium carbide (H ₂IMes)(Cl) ₂(PCy ₃)RuC (1) with the photoacid generator (PAG) [Ph ₃S][OTf] (3) under 254 nm light results in a highly efficient catalyst for ring-closing metathesis (RCM) and ring-opening metathesis polymerization (ROMP) reactions. The reactions proceed via formation of the ruthenium phosphonium alkylidene complex [(H ₂IMes)(Cl) ₂Ru=C(H)PCy ₃][OTf] as the active catalytic species. In the case of ROMP of cycloalkenes, reactions do not require addition of PAG and protonation of 1 proceeds via allylic C-H bond activation of the substrate under UV light.

Original language	English
Pages (from-to)	5634-5637
Number of pages	4
Journal	Organometallics
Volume	31
Issue number	15
DOIs	https://doi.org/10.1021/om3005965
Publication status	Published - Aug 13 2012

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Photogeneration of a phosphonium alkylidene olefin metathesis catalyst",

abstract = "Treatment of ruthenium carbide (H 2IMes)(Cl) 2(PCy 3)RuC (1) with the photoacid generator (PAG) [Ph 3S][OTf] (3) under 254 nm light results in a highly efficient catalyst for ring-closing metathesis (RCM) and ring-opening metathesis polymerization (ROMP) reactions. The reactions proceed via formation of the ruthenium phosphonium alkylidene complex [(H 2IMes)(Cl) 2Ru=C(H)PCy 3][OTf] as the active catalytic species. In the case of ROMP of cycloalkenes, reactions do not require addition of PAG and protonation of 1 proceeds via allylic C-H bond activation of the substrate under UV light.",

author = "Khalimon, {Andrey Y.} and Leitao, {Erin M.} and Piers, {Warren E.}",

year = "2012",

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journal = "Organometallics",

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T1 - Photogeneration of a phosphonium alkylidene olefin metathesis catalyst

AU - Khalimon, Andrey Y.

AU - Leitao, Erin M.

AU - Piers, Warren E.

PY - 2012/8/13

Y1 - 2012/8/13

N2 - Treatment of ruthenium carbide (H 2IMes)(Cl) 2(PCy 3)RuC (1) with the photoacid generator (PAG) [Ph 3S][OTf] (3) under 254 nm light results in a highly efficient catalyst for ring-closing metathesis (RCM) and ring-opening metathesis polymerization (ROMP) reactions. The reactions proceed via formation of the ruthenium phosphonium alkylidene complex [(H 2IMes)(Cl) 2Ru=C(H)PCy 3][OTf] as the active catalytic species. In the case of ROMP of cycloalkenes, reactions do not require addition of PAG and protonation of 1 proceeds via allylic C-H bond activation of the substrate under UV light.

AB - Treatment of ruthenium carbide (H 2IMes)(Cl) 2(PCy 3)RuC (1) with the photoacid generator (PAG) [Ph 3S][OTf] (3) under 254 nm light results in a highly efficient catalyst for ring-closing metathesis (RCM) and ring-opening metathesis polymerization (ROMP) reactions. The reactions proceed via formation of the ruthenium phosphonium alkylidene complex [(H 2IMes)(Cl) 2Ru=C(H)PCy 3][OTf] as the active catalytic species. In the case of ROMP of cycloalkenes, reactions do not require addition of PAG and protonation of 1 proceeds via allylic C-H bond activation of the substrate under UV light.

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