A Nickel-Catalyzed Route to Pyridines

McCormick, Michael M.; Duong, Hung A.; Zuo, Gang; Louie, Janis

doi:10.1021/ja0508931

Cited by 219 publications

(69 citation statements)

References 26 publications

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“…In this study, formation of a single regioisomer was observed. [52] The co-cyclotrimerization of two monoyne derivatives with a nitrile functionality (as opposed to alkyne cyclotrimerization to form benzene) proceeded smoothly (Scheme 31).…”

Section: Synthesis Of Substituted Benzene Derivativesmentioning

confidence: 99%

[2+2+2] Cycloaddition Reactions Catalyzed by Transition Metal Complexes

2006

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Recent progress in the synthesis of benzene and 1,3-cyclohexadiene derivatives, and heterocyclic compounds such as pyridines, pyridones, pyrans, pyrimidine diones, etc, has been reviewed. The general mechanistic aspects of the [2 + 2 + 2] cycloaddition reaction are discussed. The asymmetric variants of these reactions are also discussed along with the proposed models of asymmetric induction. Keywords: arenes; catalysis; cycloaddition; heterocycles; metallacycles; transition metals IntroductionThe significance and increasing popularity of [2 + 2 + 2] cycloaddition reactions is evident from the number of reviews that have recently appeared in the literature. [1][2][3] The [2 + 2 + 2] cycloaddition reaction is remarkable in terms of its ability to utilize various unsaturated substrates such as alkynes, diynes, alkenes, imines, isocyanates, isothiocyanates, and CO 2 in the synthesis of a broad variety of highly substituted cyclic molecules such as benzenes, pyridines, pyridones, 1,3-cyclohexadienes, pyrones, thiopyridones and cyclohexanes. Multisubstituted benzenes and pyridines have traditionally been synthesized by aromatic electrophilic substitution (AES) reactions and a variety of metal-mediated coupling reactions. Although, these reactions are extremely efficient, they generally involve multistep syntheses. The application of AES reactions in the synthesis of polysubstituted aromatic rings is limited by the effect of the substituent groups and, hence, it may be very difficult or even impossible to add various functionalities at a specific position on the aromatic ring. On the other hand, [2 + 2 + 2] cycloaddition reactions are extremely atom-efficient and involve the formation of several C À C bonds in a single step. Another important feature of the [2 + 2 + 2] cycloaddition reaction is tolerance of a myriad of functional groups such as alcohols, amines, alkenes, ethers, esters, halogens, and nitriles. Moreover, the availability of numerous catalytic systems that have Adv. Synth. Catal. 2006, 348, 2307 -2327 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2307 REVIEWS been efficient in tedious syntheses highlights the applicability of the [2 + 2 + 2] cycloaddition reaction. These are important requirements for the [2 + 2 + 2] cycloaddition reaction to become a universal synthetic tool for the synthesis of benzene, pyridine, and other cyclic derivatives. An important problem with the [2 + 2 + 2] cycloaddition reaction is the lack of chemoand regioselectivity observed in earlier reported reactions. However, significant effort has been focused on attaining a high degree of chemo-, regio-and even enantioselectivity with considerable success as evident from recent reports. Excellent reviews on [2 + 2 + 2] cycloaddition reactions are available. Kotha and co-workers have reviewed the synthesis of benzene derivatives by the cyclotrimerization of three alkyne functionalities utilizing transition metal systems as catalysts.[1] Their review is divided into: (a) intermolecular reactionsin which the three pi (alkyn...

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Section: Synthesis Of Substituted Benzene Derivativesmentioning

confidence: 99%

[2+2+2] Cycloaddition Reactions Catalyzed by Transition Metal Complexes

2006

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“…(242)) [1297]. Nickel catalyzed a related reaction of 1,6-, 1,7-and 1,8-diynes and nitriles to give fused bicyclic pyridines [1298]. Nickel catalyzed a cycloaddition of two alkynes and an isocyanate to give pyridones [1299].…”

Section: Cycloadditionsmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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“…Such a process has received considerable attention in recent years since it is synthetically useful, atom-economic, and environmentally benign [2]. Although a variety of stoichiometric methods have been described [3,4], catalytic systems are confined to iron [5], ruthenium [6], cobalt [7], rhodium [8], and nickel [9]. The detailed mechanism of these reactions is not yet fully established.…”

Section: Introductionmentioning

confidence: 99%