A palladium/norbornene cooperative catalysis to access N-containing bridged scaffolds

• Published in: Chemical communications (Cambridge, England) Vol. 55; no. 6; pp. 8816 - 8819
• Main Authors: Gao, Qianwen, Liu, Ze-Shui, Hua, Yu, Li, Lisha, Cheng, Hong-Gang, Cong, Hengjiang, Zhou, Qianghui
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 23.07.2019; Royal Society of Chemistry
• Subjects: amination; Aromatic compounds; Catalysis; catalytic activity; Chemical reactions; Chemistry; Chemistry, Multidisciplinary; chemoselectivity; Crystallography; Enantiomers; enantioselectivity; Iodides; Organic chemistry; organoiodine compounds; Palladium; Physical Sciences; Reagents; Scaffolds; Science & Technology; Substrates; AROMATIC FUNCTIONALIZATION; SEQUENTIAL REACTIONS; PALLADIUM; NORBORNENE; PD; ALPHA-ARYLATION; ARYL IODIDES; CATELLANI REACTION; C-H FUNCTIONALIZATION; TETRASUBSTITUTED HELICAL ALKENES
• ISSN: 1359-7345; 1364-548X; 1364-548X
• DOI: 10.1039/c9cc03126j

A palladium/norbornene cooperative catalysis promoted annulation involving an ortho -C-H amination and intramolecular Heck cascade between aryl iodides and functionalized amination reagents is reported, thereby providing a highly convergent access to the unique N-containing bridged scaffolds: hexahydro-2,6-methano-1-benzazocine. The salient features of the reaction include its broad substrate scope (with respect to aryl iodides), its high step economy, and good chemoselectivity. Preliminary studies underscore the future promise of rendering this Catellani-type annulation enantioselective. A palladium/norbornene cooperative catalysis promoted annulation involving an ortho -C-H amination and intramolecular Heck cascade between aryl iodides and functionalized amination reagents is reported, thereby providing a highly convergent access to the unique N-containing bridged scaffolds: hexahydro-2,6-methano-1-benzazocine.