Palladium-Catalyzed Cross-Coupling of Organoboron Compounds with Iodonium Salts and Iodanes
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (14) , 4720-4724
- https://doi.org/10.1021/jo960195m
Abstract
The palladium-catalyzed cross-coupling reaction of iodinanes (iodonium salts and iodanes) with organoboron compounds to form carbon−carbon bonds was achieved at ambient temperature under aqueous conditions in the absence of base. Coupling of phenylboronic acid with diphenyliodonium tetrafluoroborate in the presence of Pd(PPh3)4 (0.2 mol %) or Pd(OAc)2 (0.2 mol %) under aqueous conditions gave biphenyl in almost quantitative yield. Under the same conditions, substituted boronic acids, boronates, and trialkylboranes were readily coupled with diaryl-, alkenyl-, and alkynyliodonium salts. Finally, the iodanes ArI(OH)OTs underwent cross-coupling with boronic acids, boronates, and trialkylboranes to afford biphenyls and aryl-substituted alkenes.Keywords
This publication has 37 references indexed in Scilit:
- Palladium-Catalyzed Cross-Coupling Reactions of Organoboron CompoundsChemical Reviews, 1995
- Preparation of diorganolead dicarboxylates from aryllead triacetates: an investigation of ligand coupling in some diorganolead(IV) compoundsJournal of the Chemical Society, Perkin Transactions 1, 1994
- A Convenient Preparation of Diaryliodonium TriflatesSynthesis, 1992
- Organoboron compounds in new synthetic reactionsPure and Applied Chemistry, 1985
- Hydroboration kinetics. 3. Kinetics and mechanism of the hydroboration of alkynes with 9-borabicyclo[3.3.1]nonane dimer. Effect of structure on the reactivity of representative alkynesJournal of the American Chemical Society, 1982
- Etude du Comportement Photochimique de quelques Diaryl‐1,3‐triazènesHelvetica Chimica Acta, 1980
- 2-Alkylation Reactions of Thiophene and 1-Methylpyrrole with TrialkylboranesBulletin of the Chemical Society of Japan, 1979
- Hydroboration. 50. Hydroboration of representative alkynes with 9-borabicyclo[3.3.1]nonane - a simple synthesis of versatile vinyl bora and gem-dibora intermediatesJournal of the American Chemical Society, 1979
- Reactions of lead(IV). Part XXVIII. Oxidative coupling of methylsubstituted benzenoid compounds: formation of biaryls and diarylmethanes in trifluoroacetic acidJournal of the Chemical Society, Perkin Transactions 1, 1973
- DERIVATIVES OF PHENYLBORIC ACID, THEIR PREPARATION AND ACTION UPON BACTERIA. II. HYDROXYPHENYLBORIC ACIDS1Journal of the American Chemical Society, 1932