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Sequential O-H/C-H Bond Insertion of Phenols Initiated by the Gold(I)-Catalyzed Cyclization of 1-Bromo-1,5-enynes.
- Source :
-
Organic Letters . Apr2015, Vol. 17 Issue 8, p1982-1985. 4p. - Publication Year :
- 2015
-
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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *CHEMICAL bonds
*PHENOLS
*GOLD compounds
*RING formation (Chemistry)
*ENYNES
Subjects
Details
- Language :
- English
- ISSN :
- 15237060
- Volume :
- 17
- Issue :
- 8
- Database :
- Academic Search Index
- Journal :
- Organic Letters
- Publication Type :
- Academic Journal
- Accession number :
- 102232387
- Full Text :
- https://doi.org/10.1021/acs.orglett.5b00738