High-yielding synthesis of 2-arylacrylamides via homogeneous catalytic aminocarbonylation of α-iodostyrene and α,α′-diiodo-1,4-divinylbenzene

Takács, Attila; Farkas, Roland; Kollár, László

doi:10.1016/j.tet.2007.10.102

Cited by 29 publications

(7 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The corresponding carboxamides (5a-h and 9a-i) were formed with high chemoselectivity and isolated in moderate to good yields except for 5b ( Table 1). The low reactivity of the less basic arylamine (b) in carbonylation reactions was detected also earlier [17]. It is worth noting that even no traces of 2-ketocarboxamides, due to double carbon monoxide insertion, was detected when the catalytic mixtures were analysed by GC-MS.…”

Section: Synthesis Of 2-iodobornene (3) and 3-iodo-2-quinuclidene (8)supporting

confidence: 59%

Iodoalkene-Based Approach Towards Carboxamides of Biological Importance: Aminocarbonylation of 2-Iodobornene and 3-Iodo-2- quinuclidene

Horváth

Petz²,

Kollár

2010

LOC

View full text Add to dashboard Cite

The palladium-catalysed aminocarbonylation of 2-iodobornene and 3-iodo-2-quinuclidene, possessing iodo alkene functionality, resulted in the high-yielding synthesis of the corresponding carboxamide derivatives. The substrates were synthesised from camphor and 3-quinuclidone, respectively, via their hydrazones. The chemoselective homogeneous carbonylation reaction of synthetic value was carried out under mild reaction conditions. While the carbonylation of the 2-iodobornene was found to be a facile reaction with yields of synthetic interest, its isomer, 1-iodocamphene, formed in Wagner-Meervein rearrangement, remained intact under the same reaction conditions.

show abstract

Section: Synthesis Of 2-iodobornene (3) and 3-iodo-2-quinuclidene (8)supporting

confidence: 59%

Iodoalkene-Based Approach Towards Carboxamides of Biological Importance: Aminocarbonylation of 2-Iodobornene and 3-Iodo-2- quinuclidene

Horváth

Petz²,

Kollár

2010

LOC

View full text Add to dashboard Cite

show abstract

“…It has to be noted, that double carbon monoxide insertion was not observed under these conditions. It can be stated, based on this experiment and our previous results, that the aminocarbonylation reactions of iodoalkenes do not provide the 2-keto-carboxamide type products [ 70 , 71 ]. In the presence of substrates 2 and 3 , shorter reaction time (entries 6 and 7) was necessary to reach the complete conversion than in the case of 4 and 5 (entries 8 and 10).…”

Section: Resultsmentioning

confidence: 64%

Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation

et al. 2021

Self Cite

View full text Add to dashboard Cite

The aminocarbonylation of various alkenyl and (hetero)aryl iodides was carried out using tropane-based amines of biological importance, such as 8-azabicyclo[3.2.1]octan-3-one (nortropinone) and 3α-hydroxy-8-azabicyclo[3.2.1]octane (nortropine) as N-nucleophile. Using iodoalkenes, the two nucleophiles were selectively converted to the corresponding amide in the presence of Pd(OAc)2/2 PPh3 catalysts. In the presence of several iodo(hetero)arenes, the application of the bidentate Xantphos was necessary to produce the target compounds selectively. The new carboxamides of varied structure, formed in palladium-catalyzed aminocarbonylation reactions, were isolated and fully characterized. In this way, a novel synthetic method has been developed for the producing of N-acylnortropane derivatives of biological importance.

show abstract

“…The iodoalkenes ( 4 , 5 , 6 , 7 ) were synthesized by the modified Barton's procedure as described before. Iodobenzene was purchased from Aldrich and was used without further purification.…”

Section: Methodsmentioning

confidence: 99%

4‐Amino‐TEMPO as N‐Nucleophile in Palladium‐Catalyzed Aminocarbonylation

Gergely

Takács²,

Kollár

2016

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

Palladium‐catalyzed aminocarbonylation of iodobenzene and iodoalkenes (1‐iodocyclohexene, 4‐tert‐butyl‐1‐iodocyclohexene, α‐iodostyrene, 17‐iodoandrost‐16‐ene) was carried out using a free radical (4‐amino‐TEMPO) for the first time. Its reduced form (4‐amino‐2,2,6,6‐tetramethylpiperidine) was also used as N‐nucleophile. The free radical was partially reduced under aminocarbonylation conditions; however, the isolation of carbonylated products bearing a stable radical moiety was successfully accomplished. It was proved that the reduction of the 1‐oxyl functionality took place to higher extent when more severe conditions (40 bar CO pressure) were used. The mixture of carboxamide and 2‐ketocarboxamide products was obtained using iodobenzene because of single and double carbon monoxide insertion, respectively. In turn, carboxamide derivatives were formed exclusively when iodoalkenes were used as substrates.

show abstract

High-yielding synthesis of 2-arylacrylamides via homogeneous catalytic aminocarbonylation of α-iodostyrene and α,α′-diiodo-1,4-divinylbenzene

Cited by 29 publications

References 33 publications

Iodoalkene-Based Approach Towards Carboxamides of Biological Importance: Aminocarbonylation of 2-Iodobornene and 3-Iodo-2- quinuclidene

Iodoalkene-Based Approach Towards Carboxamides of Biological Importance: Aminocarbonylation of 2-Iodobornene and 3-Iodo-2- quinuclidene

Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation

4‐Amino‐TEMPO as N‐Nucleophile in Palladium‐Catalyzed Aminocarbonylation

Contact Info

Product

Resources

About