Synthesis of Functionalized Organotrifluoroborates via the 1,3-Dipolar Cycloaddition of Azides
- 1 June 2006
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 8 (13) , 2767-2770
- https://doi.org/10.1021/ol060826r
Abstract
We have successfully prepared potassium azidoalkyltrifluoroborates from the corresponding halogen compounds in 94−98% yields through a nucleophilic substitution reaction with NaN3. In the presence of various alkynes and Cu(I) as a catalyst, these azidotrifluoroborates easily formed 1,4-disubstituted organo-[1,2,3]-triazol-1-yl-trifluoroborates in 85−98% yields. This method was then developed into a facile one-pot synthesis for the preparation of various organo-[1,2,3]-triazol-1-yl-trifluoroborates using haloalkyltrifluoroborates as the starting materials.Keywords
This publication has 20 references indexed in Scilit:
- Synthesis of Functionalized Organotrifluoroborates via HalomethyltrifluoroboratesOrganic Letters, 2006
- 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
- Stereoselective Suzuki−Miyaura Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates with Alkenyl BromidesThe Journal of Organic Chemistry, 2005
- Hydroboration with Pyridine Borane at Room TemperatureJournal of the American Chemical Society, 2005
- Regiospecific Functionalization of Methyl C−H Bonds of Alkyl Groups in Reagents with Heteroatom FunctionalityJournal of the American Chemical Society, 2004
- Allylation and highly diastereoselective syn or anti crotylation of N-toluenesulfonylimines using potassium allyl- and crotyltrifluoroboratesChemical Communications, 2004
- A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal AlkynesAngewandte Chemie International Edition in English, 2002
- Potassium Alkenyl- and Aryltrifluoroborates: Stable and Efficient Agents for Rhodium-Catalyzed Addition to Aldehydes and EnonesOrganic Letters, 1999