Annulation of Aromatic Imines via Directed C-H BondActivation
A directed C-H bond activation approach to the synthesis of indans, tetralins, dihydrofurans, dihydroindoles, and other polycyclic aromatic compounds is presented. Cyclization of aromatic ketimines and aldimines containing alkenyl groups tethered at the meta position relative to the imine directing group has been achieved using (PPh{sub 3}){sub 3}RhCl (Wilkinson's catalyst). The cyclization of a range of aromatic ketimines and aldimines provides bi- and tricyclic ring systems with good regioselectivity. Different ring sizes and substitution patterns can be accessed through the coupling of monosubstituted, 1,1- or 1,2-disubstituted, and trisubstituted alkenes bearing both electron-rich and electron-deficient functionality.
- Research Organization:
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Sponsoring Organization:
- USDOE Director. Office of Science. Office of Basic EnergySciences. Chemical Sciences Geosciences and BiosciencesDivision
- DOE Contract Number:
- DE-AC02-05CH11231
- OSTI ID:
- 908468
- Report Number(s):
- LBNL-59474; JOCEAH; R&D Project: 402101; BnR: KC0302010; TRN: US200722%%649
- Journal Information:
- Journal of Organic Chemistry, Vol. 70; Related Information: Journal Publication Date: 2005; ISSN 0022-3263
- Country of Publication:
- United States
- Language:
- English
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