13021-19-7Relevant articles and documents
Single and double Suzuki-Miyaura couplings with symmetric dihalobenzenes
Sinclair, David J.,Sherburn, Michael S.
, p. 3730 - 3733 (2005)
(Chemical Equation Presented) m- or p-diiodobenzene undergoes selective double coupling reactions with arylboronic acids and esters. Selectivity for double coupling over single coupling is remarkably strong: even with a diiodobenzene:monoboronic acid ratio of 10:1, the products of double coupling are formed in good yields. Steric hindrance and electronic influences of the boronic acid or ester, and reaction conditions do not appear to impact significantly upon the outcome of the reaction. In contrast, m- and p-dibromobenzenes undergo single couplings with aryl boronic acids with high selectivity.
Efficient synthesis of substituted terphenyls by Suzuki coupling reaction
Chaumeil, He?le?ne,Le Drian, Claude,Defoin, Albert
, p. 757 - 760 (2002)
The Suzuki cross-coupling reactions of phenyl-1,4-diboronic acid bis-pinacol ester with a range of aryl halides are reported. The reaction proceeded smoothly, even with sterically hindered aryl halides, to give symmetrical terphenyls often quantitatively.
Palladium (II)–Salan Complexes as Catalysts for Suzuki–Miyaura C–C Cross-Coupling in Water and Air. Effect of the Various Bridging Units within the Diamine Moieties on the Catalytic Performance
Bunda, Szilvia,Joó, Ferenc,Kathó, ágnes,Udvardy, Antal,Voronova, Krisztina
supporting information, (2020/09/18)
Water-soluble salan ligands were synthesized by hydrogenation and subsequent sulfonation of salens (N,N’-bis(slicylidene)ethylenediamine and analogues) with various bridging units (linkers) connecting the nitrogen atoms. Pd (II) complexes were obtained in reactions of sulfosalans and [PdCl4]2?. Characterization of the ligands and complexes included extensive X-ray diffraction studies, too. The Pd (II) complexes proved highly active catalysts of the Suzuki–Miyaura reaction of aryl halides and arylboronic acid derivatives at 80 ?C in water and air. A comparative study of the Pd (II)–sulfosalan catalysts showed that the catalytic activity largely increased with increasing linker length and with increasing steric congestion around the N donor atoms of the ligands; the highest specific activity was 40,000 (mol substrate) (mol catalyst × h)?1. The substrate scope was explored with the use of the two most active catalysts, containing 1,4-butylene and 1,2-diphenylethylene linkers, respectively.
Aryl/heteroaryl pentafluorobenzenesulfonates (ArOPFBs): New electrophilic coupling partners for room temperature Suzuki-Miyaura cross-coupling reactions
Joseph, Jayan T.,Sajith, Ayyiliath M.,Ningegowda, Revanna C.,Nagaraj, Archana,Rangappa,Shashikanth, Sheena
, p. 5106 - 5111 (2015/08/06)
The first cross-coupling reaction between aryl/heteroaryl pentafluorobenzenesulfonates and aryl/heteroaryl boronic acids under mild conditions is described. The successful synthesis of highly ortho substituted biaryls and high chemoselectivity of these bench stable intermediates over tosylates, triflates, mesylates, and chlorides increases its scope as a valuable cross-coupling partner. The generality of this protocol was further extended to other boron containing nucleophiles (boronates, trifluoroborates) and alkyl boronic acids.
