Journal
CHEMICAL COMMUNICATIONS
Volume 55, Issue 63, Pages 9267-9270Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9cc04152d
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Funding
- JSPS KAKENHI [JP18H04234, JP18K05116, JP19H02707]
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Transition metal-free hydroarylation of unactivated alkynes was achieved by combining a Bronsted acid catalyst and a two-phase solvent system consisting of 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) and cyclohexane. This protocol is applicable to a wide variety of 2-alkynylbiaryls which leads to the synthesis of substituted phenanthrenes via 6-endo-selective ring closure. The biphasic system achieves highly efficient ring closure by appropriate separation of cationic intermediates from neutral compounds. The vinyl carbocation intermediates are stabilised in the HFIP phase, while the substrates and products are distributed in the cyclohexane phase to suppress intermolecular side reactions.
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