Linchpin Synthons: Metalation of Aryl Bromides Bearing a Potassium Trifluoroborate Moiety
- 19 August 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 71 (19) , 7491-7493
- https://doi.org/10.1021/jo061324u
Abstract
Aryl bromides bearing a potassium trifluoroborate moiety were subjected to lithium−halogen exchange at low temperature using a variety of alkyllithium reagents. A number of different electrophiles were evaluated in their reactions with the aryllithiums produced therein. Under carefully optimized conditions, potassium bromophenyl trifluoroborates afforded good to excellent yields of the corresponding alcohols (64−94% isolated yield) when aldehydes or ketones were used as the electophilic partner. Esters were unfortunately found to be unreactive.Keywords
This publication has 20 references indexed in Scilit:
- One-Pot Synthesis of Trisubstituted Conjugated Dienes via Sequential Suzuki−Miyaura Cross-Coupling with Alkenyl- and AlkyltrifluoroboratesThe Journal of Organic Chemistry, 2006
- Palladium(0)-Catalyzed Synthesis of Chiral Ene-allenes Using Alkenyl TrifluoroboratesThe Journal of Organic Chemistry, 2006
- Suzuki−Miyaura Cross-Coupling Reactions of Aryl Tellurides with Potassium Aryltrifluoroborate SaltsThe Journal of Organic Chemistry, 2005
- Preparation and Selective Reactions of Mixed Bimetallic Aromatic and Heteroaromatic Boron–Magnesium ReagentsAngewandte Chemie International Edition in English, 2005
- Highly Functionalized Organomagnesium Reagents Prepared through Halogen–Metal ExchangeAngewandte Chemie International Edition in English, 2003
- Selective Halogen−Magnesium Exchange Reaction via Organomagnesium Ate ComplexThe Journal of Organic Chemistry, 2001
- Low-Temperature Formation of Functionalized Grignard Reagents from Direct Oxidative Addition of Active Magnesium to Aryl BromidesThe Journal of Organic Chemistry, 2000
- Potassium Alkenyl- and Aryltrifluoroborates: Stable and Efficient Agents for Rhodium-Catalyzed Addition to Aldehydes and EnonesOrganic Letters, 1999
- Aromatic organolithium reagents bearing electrophilic groups. Preparation by halogen-lithium exchangeAccounts of Chemical Research, 1982
- Preliminary studies of the mechanism of metal-halogen exchange. The kinetics of reaction of n-butyllithium with substituted bromobenzenes in hexane solutionJournal of the American Chemical Society, 1982