2022
DOI: 10.1021/acs.joc.1c03044
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Redox-Neutral Ru(0)-Catalyzed Alkenylation of 2-Carboxaldimine-heterocyclopentadienes

Abstract: A new Ru 3 (CO) 12 -catalyzed directed alkenylation of 2-carboxaldimine-heterocyclopentadienes has been accomplished. This process allows to couple furan, pyrrole, indole and thiophene 2-carboxaldimines with electron-poor alkenes such as acrylates, vinylsulfones, and styrenes. This regio-and chemoselective oxidative C-H coupling does not require the presence of an additional sacrificial oxidant. Density functional theory (DFT) calculations allowed to propose a mechanism and unveiled the nature of the H 2 accep… Show more

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Cited by 15 publications
(20 citation statements)
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“…Commercially available 2-iodopropane ( 2a ), cyclohexyl iodide ( 2b ), and 1,1,1-trifluoro-3-iodopropane ( 2c ) were distilled prior to use. Reagents shown below were synthesized according to literature procedures: N -methyl-1-phenylmethanimine ( 1a ), N -(2-methoxyethyl)-1-phenylmethanimine ( 1b ), 1-(3-methoxyphenyl)- N -methylmethanimine ( 1c ), methyl 2-(benzylideneamino)­acetate ( 1d ), 2-(benzylideneamino)- N , N -dimethylethan-1-amine ( 1e ), N ,1-diphenylmethanimine ( 1f ), N -allyl-1-phenylmethanimine ( 1g ), N -benzyl-1-phenylmethanimine ( 1h ), N -cyclopropyl-1-phenylmethanimine ( 1i ), 1-(4-chlorophenyl)- N -phenylmethanimine ( 4a ), 1-(4-methoxyphenyl)- N -phenylmethanimine ( 4b ), N -(4-bromophenyl)-1-phenylmethanimine ( 4c ), 1-(4-methoxyphenyl)- N -(p-tolyl)­methanimine ( 4d ), N ,1-bis­(4-methoxyphenyl)­methanimine ( 4e ), 1-(furan-2-yl)- N -(4-methoxyphenyl)­methanimine ( 4f ), N -benzylidene-4-methylbenzenesulfonamide ( 6 ), tert -butyl 4-iodopiperidine-1-carboxylate ( 2d ), (3-iodobutyl)­benzene ( 2e ), (3-iodopropyl)­benzene ( 2f ), 4-iodobut-1-ene ( 2g ), ethyl 4-iodobutanoate ( 2h ), 4-iodobutanenitrile ( 2i ), (iodomethyl)­trimethylsilane ( 2j ), 4-iodobutyl pivalate ( 2k ), iodocyclooctane ( 2f ), 1-iodo-2-methylpropane ( 2m ), 5-iodopent-1-ene ( 2n ), 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate ( 8 ), 2,4,6-tris­(diphenylamino)-3,5-difluorobenzonitrile (3DPA2FBN) …”
Section: Methodsmentioning
confidence: 99%
“…Commercially available 2-iodopropane ( 2a ), cyclohexyl iodide ( 2b ), and 1,1,1-trifluoro-3-iodopropane ( 2c ) were distilled prior to use. Reagents shown below were synthesized according to literature procedures: N -methyl-1-phenylmethanimine ( 1a ), N -(2-methoxyethyl)-1-phenylmethanimine ( 1b ), 1-(3-methoxyphenyl)- N -methylmethanimine ( 1c ), methyl 2-(benzylideneamino)­acetate ( 1d ), 2-(benzylideneamino)- N , N -dimethylethan-1-amine ( 1e ), N ,1-diphenylmethanimine ( 1f ), N -allyl-1-phenylmethanimine ( 1g ), N -benzyl-1-phenylmethanimine ( 1h ), N -cyclopropyl-1-phenylmethanimine ( 1i ), 1-(4-chlorophenyl)- N -phenylmethanimine ( 4a ), 1-(4-methoxyphenyl)- N -phenylmethanimine ( 4b ), N -(4-bromophenyl)-1-phenylmethanimine ( 4c ), 1-(4-methoxyphenyl)- N -(p-tolyl)­methanimine ( 4d ), N ,1-bis­(4-methoxyphenyl)­methanimine ( 4e ), 1-(furan-2-yl)- N -(4-methoxyphenyl)­methanimine ( 4f ), N -benzylidene-4-methylbenzenesulfonamide ( 6 ), tert -butyl 4-iodopiperidine-1-carboxylate ( 2d ), (3-iodobutyl)­benzene ( 2e ), (3-iodopropyl)­benzene ( 2f ), 4-iodobut-1-ene ( 2g ), ethyl 4-iodobutanoate ( 2h ), 4-iodobutanenitrile ( 2i ), (iodomethyl)­trimethylsilane ( 2j ), 4-iodobutyl pivalate ( 2k ), iodocyclooctane ( 2f ), 1-iodo-2-methylpropane ( 2m ), 5-iodopent-1-ene ( 2n ), 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate ( 8 ), 2,4,6-tris­(diphenylamino)-3,5-difluorobenzonitrile (3DPA2FBN) …”
Section: Methodsmentioning
confidence: 99%
“…(Scheme 31). [117] It is interesting to note that this dehydrogenative coupling does not require the presence of a sacrificial hydrogen acceptor, as the excess of acrylate plays this role. The reaction mechanism, postulated on the basis of DFT computations, involves a regioselective carboruthenation of the acrylate, followed by dehydroruthenation.…”
Section: Selective Functionalization Of Furfural Derivativesmentioning
confidence: 99%
“…In contrast, C3-functionalizations of the formyl-furan unit via directing groups, as well as C4-functionalizations have been much less studied. [19,20] Within the framework of a large project oriented towards the selective formation of new bonds from furfural derivatives without changing the redox state of the aldehyde function, we have developed a number of directed Ru(0)-catalyzed C3-3 functionalizations of furfurylimines, such as alkylation, [21] arylation, [22] alkenylation [23] and acylation, [24] as well as an Ir-catalyzed directed C3-silylation (Scheme 1a). [25] These batch processes rely on the use of a homogeneous metal catalyst at elevated temperatures necessary to cleave the C3-H bond by oxidative addition.…”
Section: Introductionmentioning
confidence: 99%