title: Sequential O-H/C-H bond insertion of phenols initiated by the gold(I)-catalyzed cyclization of 1-bromo-1,5-enynes.
abstract: The development of a sequential O-H/C-H bond functionalization of phenols initiated by the cationic gold(I)-catalyzed cyclization of 1-bromo-1,5-enynes to produce (2-bromocyclopent-2-en-1-yl)phenols is reported. This unprecedented domino transformation efficiently proceeds under mild conditions (5 mol % of (t-Bu)3PAuNTf2, CH2Cl2, 0-23 °C) via an intermediate aryl alkyl ether which collapses at ambient temperature to undergo a 1,2-hydride shift followed by C-H insertion of the phenol.
authors.affiliation: Department of Chemistry and Pharmacy, Ludwig-Maximilians-University Munich, Butenandtstrasse 5-13, 81377 Munich, Germany.
authors.forename: Klaus
authors.initials: K
authors.lastname: Speck
authors.affiliation: Department of Chemistry and Pharmacy, Ludwig-Maximilians-University Munich, Butenandtstrasse 5-13, 81377 Munich, Germany.
authors.forename: Konstantin
authors.initials: K
authors.lastname: Karaghiosoff
authors.affiliation: Department of Chemistry and Pharmacy, Ludwig-Maximilians-University Munich, Butenandtstrasse 5-13, 81377 Munich, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Magauer
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D000480:Alkynes; D010636:Phenols; D006046:Gold