ChemInform Abstract: Gold‐Catalyzed 6‐Exo‐Dig Cycloisomerization: A Versatile Approach to Functionalized Phenanthrenes.
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Abstract Various functionalized phenanthrenes are synthesized with good functional group tolerance by a general and practical method starting from readily available o‐propargyl biaryls under mild reaction conditions.Keywords:
Phenanthrenes
Cycloisomerization
Propargyl
Functional group
Reaction conditions
Abstract For Abstract see ChemInform Abstract in Full Text.
Phenanthrenes
Cycloisomerization
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Abstract A novel gold‐catalyzed 6‐ exo ‐ dig cycloisomerization of o ‐propargylbiaryls has been developed that provides ready access to functionalized phenanthrenes in largely good to excellent yields. Notable features of this method are readily available starting materials, mild reaction conditions, and broad substrate scope.
Cycloisomerization
Phenanthrenes
Scope (computer science)
Dig
Reaction conditions
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[reaction: see text] 1,6-Enynes and allyl propargyl ethers undergo a cobalt-catalyzed formal 5-endo-dig cyclization to form vinyl cyclopentenes and dihydrofurans, respectively. The use of equimolar amounts of dicobalt octacarbonyl and trimethyl phosphite affords optimum yields and improved selectivity for cycloisomerization vs alkene isomerization.
Cycloisomerization
Propargyl
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Readily available o'-alkenyl-o-alkynylbiaryls, a particular type of 1,7-enynes, undergo a selective cycloisomerization reaction in the presence of a gold(I) catalyst to give interesting phenanthrene and dihydrophenanthrene derivatives in high yields. The solvent used provokes a switch in the evolution of the gold intermediate and plays a key role in the reaction outcome.
Cycloisomerization
Phenanthrenes
Biphenyl
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Abstract Various functionalized phenanthrenes are synthesized with good functional group tolerance by a general and practical method starting from readily available o‐propargyl biaryls under mild reaction conditions.
Phenanthrenes
Cycloisomerization
Propargyl
Functional group
Reaction conditions
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Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Cycloisomerization
Propargyl
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Abstract Ruthenium‐catalyzed cycloisomerization of 2‐ethynylbiaryls was investigated to identify an optimal ruthenium catalyst system. A combination of [η 6 ‐( p ‐cymene)RuCl 2 (PR 3 )] and two equivalents of AgPF 6 effectively converted 2‐ethynylbiphenyls into phenanthrenes in chlorobenzene at 120 °C over 20 h. Moreover, 2‐ethynylheterobiaryls were found to be favorable substrates for this ruthenium catalysis, thus achieving the cycloisomerization of previously unused heterocyclic substrates. Moreover, several control experiments and DFT calculations of model complexes were performed to propose a plausible reaction mechanism.
Cycloisomerization
Phenanthrenes
Chlorobenzene
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Abstract Ortho‐alkynyl biaryls react in the presence of catalytic amount of Brønsted acids to give phenanthrenes in high yields under mild conditions. The activity and selectivity of this transformation are governed by the substitution pattern of the diarylalkyne moiety. Selectivity shifts are observed between the carbophilic Lewis and Brønsted acid‐catalyzed cycloisomerization involving alkyne activation. magnified image
Cycloisomerization
Phenanthrenes
Moiety
Brønsted–Lowry acid–base theory
Alkyne
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Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
Cycloisomerization
Propargyl
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Abstract Numerous functionalized phenanthrenes are obtained via In(III)‐catalyzed electrophile‐promoted nucleophilic cyclization of o‐propargylbiaryls.Various functionalized groups are tolerated on the alkynyl carbon.
Phenanthrenes
Cycloisomerization
Dig
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