Potassium (1‐Organo‐1H‐1, 2, 3‐triazol‐4‐yl)trifluoroborates from Ethynyltrifluoro­borate through a Regioselective One‐Pot Cu‐Catalyzed Azide–Alkyne Cycloaddition Reaction. Issue 19 (17th May 2013)

• Record Type: Journal Article
• Authors: Kim, Taejung; Song, Jung Ho; Jeong, Kyu Hyuk; Lee, Seokjoon; Ham, Jungyeob
• Is Part Of: European journal of organic chemistry. Issue 19(2013)
• Page Start: 3992
• Page End: 3996
• Publication Date: 2013-05-17
• Subjects: Copper -- Click chemistry -- Bor­on -- Nitrogen heterocycles -- Cross‐cou­pling; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300365
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A novel series of 1, 4‐disubstituted 1, 2, 3‐triazole‐containing potassium trifluoroborates were prepared in good to excellent yields from the corresponding organohalides and potassium ethynyltrifluoroborate through a regioselective one‐pot Cu‐catalyzed azide–alkyne cycloaddition (CuAAC) reaction. Further Suzuki–Miyaura cross‐coupling of these (organo‐1, 2, 3‐triazol‐4‐yl)trifluoroborates with aryl and alkenyl bromides by using a PdCl2 (dppf)· CH2 Cl2 /TBAB [dppf = 1, 1′‐bis(diphenylphosphanyl)ferrocene, TBAB = tetrabutylammonium bromide] system under microwave irradiation was explored. Abstract : The preparation of potassium (1‐organo‐1 H ‐1, 2, 3‐triazol‐4‐yl)trifluoroborates from potassium ethynyltrifluoroborate and alkyl or aryl halides by employing a regioselective one‐pot Cu‐catalyzed azide–alkyne cycloaddition (CuAAC) is elaborated. This strategy allows unrestricted access to an infinite variety of 1, 4‐disubstituted 1, 2, 3‐triazoles.