Solvent‐Free Buchwald–Hartwig (Hetero)arylation of Anilines, Diarylamines, and Dialkylamines Mediated by Expanded‐Ring N‐Heterocyclic Carbene Palladium Complexes. Issue 10 (15th March 2016)

• Record Type: Journal Article
• Authors: Topchiy, Maxim A.; Dzhevakov, Pavel B.; Rubina, Margarita S.; Morozov, Oleg S.; Asachenko, Andrey F.; Nechaev, Mikhail S.
• Is Part Of: European journal of organic chemistry. Issue 10(2014)
• Page Start: 1908
• Page End: 1914
• Publication Date: 2016-03-15
• Subjects: Green chemistry -- Cross‐coupling -- Amination -- Palladium -- Carbene ligands; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501616
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A highly efficient solvent‐free protocol for the Buchwald–Hartwig (hetero)arylation of anilines, diarylamines, and dialkylamines mediated by the expanded‐ring N‐heterocyclic carbene palladium complex (THP‐Dipp)Pd(cinn)Cl [THP‐Dipp = 1, 3‐bis(2, 6‐diisopropylphenyl)‐3, 4, 5, 6‐tetrahydropyrimidin‐2‐ylidene; cinn = cinnamyl, 3‐phenylallyl] was developed. The catalytic protocol was efficient for the coupling of amines and (hetero)aryl chlorides and bromides bearing donor, acceptor, and bulky substituents. Abstract : The six‐membered‐ring cyclic diaminocarbene palladium complex (THP‐Dipp)Pd(cinn)Cl [THP‐Dipp = 1, 3‐bis(2, 6‐diisopropylphenyl)‐3, 4, 5, 6‐tetrahydropyrimidin‐2‐ylidene; cinn = cinnamyl, 3‐phenylallyl] serves as an excellent precatalyst for the coupling of anilines, diarylamines, and dialkylamines with (hetero)aryl chlorides and bromides. RuPhos = 2‐dicyclohexylphosphino‐2′, 6′‐diisopropoxybiphenyl.