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Ruthenium-Catalyzed Dimerization of 1,1-Diphenylpropargyl Alcohol to a Hydroxybenzocyclobutene and Related Reactions
by
Takao Ikariya
, Hoang Nguyen
, Naoto Tashima
, Shigeki Kuwata
in
Alcohol
/ alkyne
/ benzocyclobutene
/ Catalysts
/ Crystallography
/ C–H cleavage
/ Dehydrogenation
/ Dimerization
/ Inorganic chemistry
/ Isoprene
/ Organic chemistry
/ Propargyl alcohol
/ QD146-197
/ Reaction mechanisms
/ Ruthenium
/ Ruthenium compounds
/ ruthenium; alkyne; propargyl alcohol; C–H cleavage; benzocyclobutene
/ X-ray crystallography
/ X-rays
2017
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Ruthenium-Catalyzed Dimerization of 1,1-Diphenylpropargyl Alcohol to a Hydroxybenzocyclobutene and Related Reactions
by
Takao Ikariya
, Hoang Nguyen
, Naoto Tashima
, Shigeki Kuwata
in
Alcohol
/ alkyne
/ benzocyclobutene
/ Catalysts
/ Crystallography
/ C–H cleavage
/ Dehydrogenation
/ Dimerization
/ Inorganic chemistry
/ Isoprene
/ Organic chemistry
/ Propargyl alcohol
/ QD146-197
/ Reaction mechanisms
/ Ruthenium
/ Ruthenium compounds
/ ruthenium; alkyne; propargyl alcohol; C–H cleavage; benzocyclobutene
/ X-ray crystallography
/ X-rays
2017
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Ruthenium-Catalyzed Dimerization of 1,1-Diphenylpropargyl Alcohol to a Hydroxybenzocyclobutene and Related Reactions
by
Takao Ikariya
, Hoang Nguyen
, Naoto Tashima
, Shigeki Kuwata
in
Alcohol
/ alkyne
/ benzocyclobutene
/ Catalysts
/ Crystallography
/ C–H cleavage
/ Dehydrogenation
/ Dimerization
/ Inorganic chemistry
/ Isoprene
/ Organic chemistry
/ Propargyl alcohol
/ QD146-197
/ Reaction mechanisms
/ Ruthenium
/ Ruthenium compounds
/ ruthenium; alkyne; propargyl alcohol; C–H cleavage; benzocyclobutene
/ X-ray crystallography
/ X-rays
2017
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Ruthenium-Catalyzed Dimerization of 1,1-Diphenylpropargyl Alcohol to a Hydroxybenzocyclobutene and Related Reactions
Journal Article
Ruthenium-Catalyzed Dimerization of 1,1-Diphenylpropargyl Alcohol to a Hydroxybenzocyclobutene and Related Reactions
2017
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Overview
Propargyl alcohol is a useful synthon in synthetic organic chemistry. We found that the ruthenium(II) complex [Cp*RuCl(diene)] (Cp* = η5-C5Me5; diene = isoprene or 1,5-cyclooctadiene (cod)) catalyzes dimerization of 1,1-diphenylprop-2-yn-1-ol (1,1-diphenylpropargyl alcohol, 1a) at room temperature to afford an alkylidenebenzocyclobutenyl alcohol 2a quantitatively. Meanwhile, a stoichiometric reaction of the related hydrido complex [Cp*RuH(cod)] with 1a at 50 °C led to isolation of a ruthenocene derivative 4 bearing a cyclopentadienyl ring generated by dehydrogenative trimerization of 1a. Detailed structures of 2a and 4 were determined by X-ray crystallography. The reaction mechanisms for the formation of 2a and 4 were proposed.
Publisher
MDPI AG
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