title: Efficient synthesis of sterically hindered arenes bearing acyclic secondary alkyl groups by Suzuki-Miyaura cross-couplings.
abstract: Bulky P,P=O ligands were designed to inhibit isomerization and reduction side reactions during the cross coupling between sterically hindered aryl halides and alkylboronic acids. Suzuki-Miyaura cross-couplings between di-ortho-substituted aryl bromides and acyclic secondary alkylboronic acids have been achieved with high yields. The method has also enabled the preparation of ortho-alkoxy di-ortho-substituted arenes bearing isopropyl groups in excellent yields. The utility of the synthetic method has been demonstrated in a late-stage modification of estrone and in the application to a new synthetic route toward gossypol.
authors: State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai 200032 (China).
authors: Chengxi
authors: C
authors: Li
authors: Tianyu
authors: T
authors: Chen
authors: Bowen
authors: B
authors: Li
authors: Guolan
authors: G
authors: Xiao
authors: Wenjun
authors: W
authors: Tang
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry; D018360:Crystallography, X-Ray; D007536:Isomerism; D008024:Ligands; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry
chemical_list: D001555:Benzene Derivatives; D001897:Boronic Acids; D056831:Coordination Complexes; D008024:Ligands; D010165:Palladium
keywords: aryl-alkyl cross-coupling; boronic acids; isopropyl arenes; ligand design; reductive elimination