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Development of Unimolecular Tetrakis(piperidin‐4‐ol) as a Ligand for Suzuki–Miyaura Cross‐Coupling Reactions: Synthesis of Incrustoporin and Preclamol
Author(s) -
Nallasivam Jothi L.,
Fernandes Rodney A.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500353
Subject(s) - chemistry , combinatorial chemistry , domino , ligand (biochemistry) , coupling reaction , suzuki reaction , heck reaction , organic chemistry , catalysis , palladium , biochemistry , receptor
A domino aza‐Cope/aza‐Prins cascade enabled the synthesis of a new class of 4‐hydroxypiperidine‐appended mono, bis, tris, and tetrakis unimolecular compounds that served as efficient ligands to catalyze Suzuki–Miyaura cross‐coupling reactions under aerobic conditions. Various biaryls, terphenyls, and heterocyclic biphenyls were obtained in good to excellent yields. The ligands were also capable of catalyzing the Heck–Mizoroki reaction. As an application, the Suzuki–Miyaura coupling reaction was used in the synthesis of incrustoporin, its analogs, and the drug molecule preclamol.