181717-12-4Relevant articles and documents
Cyclization of η3-benzylpalladium intermediates derived from carbene insertion
Gutman, Eugene S.,Arredondo, Vanessa,Van Vranken, David L.
supporting information, p. 5498 - 5501 (2015/01/09)
Migratory insertion of benzylidene carbene ligands into arylpalladium(II) species generates η3-benzylpalladium intermediates that can cyclize to generate five- and six-membered rings with new sp3 centers. The reaction tolerates a ran
Synthesis of indolines via a domino Cu-catalyzed amidation/cyclization reaction
Minatti, Ana,Buchwald, Stephen L.
supporting information; experimental part, p. 2721 - 2724 (2009/05/27)
(Chemical Equation Presented) A highly efficient one-pot procedure for the synthesis of indolines and their homologues based on a domino Cu-catalyzed amidation/nucleophilic substitution reaction has been developed. Substituted 2-iodophenethyl mesylates and related compounds afforded the corresponding products in excellent yields. No erosion of optical purity was observed when transforming enantiomerically pure mesylates under the reaction conditions.
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.