115860-48-5Relevant articles and documents
Carbopalladation of nitriles: Synthesis of benzocyclic ketones and cyclopentenones via Pd-catalyzed cyclization of ω-(2-iodoaryl)alkanenitriles and related compounds
Pletnev, Alexandre A.,Larock, Richard C.
, p. 9428 - 9438 (2007/10/03)
An efficient procedure for the synthesis of 2,2-disubstituted benzocyclic ketones by intramolecular carbopalladation of nitriles has been developed. The cyclization of substituted 3-(2-iodoaryl)-propanenitriles affords indanones in high yields. The reaction is compatible with a wide variety of functional groups. This methodology has been extended to the synthesis of tetralones and cyclopentenones.
Controlled double-bond migration in palladium-catalyzed intramolecular arylation of enamidines
Ripa, Lena,Hallberg, Anders
, p. 7147 - 7155 (2007/10/03)
Palladium-catalyzed intramolecular cyclization of N-(N′-tert-butylformimidoyl)-6-[2-(2-iodophenyl)-ethyl]-1,2,3,4- tetrahydropyridine (1a) and N-(N′-tert-butylformimidoyl)-6-[3-(2-iodophenyl)propyl]-1,2,3,4- tetrahydropyridine (1b) respectively results in formation of spiro compounds 1′-(N-tert-butylformimidoyl)-3′,4′-dihydrospiro[indan-1, 2′(1′H)-pyridine] (4a), 1′-(N-tert-butylformimidoyl)-1′,6′-dihydrospiro[indan-1, 2′(3′H)-pyridine] (5a), and 1′-(N-tert-butylformimidoyl)-5′,6′-dihydrospiro[indan-1, 2′(1′H)-pyridine] (6a) and 1′-(N-tert-butylformimidoyl)-3,3′,4,4′- tetrahydrospiro[naphthalene-1(2H),2′(1′H)-pyridine] (4b), 1′-(N-tert-butylformimidoyl)-1′,3,4,6′- tetrahydrospiro[naphthalene-1(2H),2′(3′H)-pyridine] (5b), and 1′-(N-tert-butylformimidoyl)-3,4,5′,6′- tetrahydrospiro[naphthalene-1(2H),2′(1′H)-pyridine] (6b). The double-bond migration process can be controlled, and any of the three double-bond isomers can be prepared by employing proper ligands. A combination of BINAP and the amidine function was required to obtain the isomers 5a and 5b with the double bond in the homoallylic position relative to the aryl group. An electrospray ionization mass spectrometric study was conducted to support suggested reaction intermediates.