An Expeditious and Environmentally‐Benign Approach to 2‐Aryl/Heteroaryl Selenopyridines via Ruthenium Catalyzed [2+2+2] Cycloadditions

Kalaramna, Pratibha; Bhatt, Divya; Sharma, Himanshu; Goswami, Avijit

doi:10.1002/ejoc.201900664

Cited by 14 publications

(10 citation statements)

References 49 publications

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“…Over the past decade, aryl selenocyanates (ArSeCN) have attracted considerable attention since they displayed biological activity [2] and found wide applications in organic synthesis. For example, aryl selenocyanates have appeared as an important organoselenium reagent to construct various organic selenium compounds including monoselenides, [3a–e] diselenides, [3f,g] trifluoromethyl (difluoromethyl) selenides, [3h,i] selenoesters [3j] and selenium‐containing ligands [3k] . In some cases, aryl selenocyanates could serve as a useful bifunctional reagent for the direct cyanoselenenylation of unsaturated C−C bonds [4]…”

Section: Methodsmentioning

confidence: 99%

Metal‐Free Synthesis of Aryl Selenocyanates and Selenaheterocycles with Elemental Selenium

Zhang

Huang

Zhou

et al. 2020

Chemistry A European J

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Section: Methodsmentioning

confidence: 99%

Metal‐Free Synthesis of Aryl Selenocyanates and Selenaheterocycles with Elemental Selenium

Zhang

Huang

Zhou

et al. 2020

Chemistry A European J

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“… The same year, Goswami reported related [2+2+2] cycloadditions of 1,6-diynes with 3-thiocyanatoindoles to form 3-(2-thiopyridyl)indoles (Scheme ). Later in 2019, Goswami described analogous [2+2+2] cycloadditions of 1,6-diynes with selenocyanates or aryl cyanates to form selenopyridines , and 2-aryloxypyridines, respectively (not shown). In 2018, in [2+2+2] cycloadditions of 1,6-diynes with acetylenic nitriles, Goswami found that neutral Cp*Ru catalysts provide benzonitriles ( vide supra , Scheme ), whereas cationic Cp*Ru catalysts (generated in situ from Cp*RuCl(cod) and AgOTf) provide 2-alkynylpyridines (Scheme ).…”

Section: Six-membered Ring Formationmentioning

confidence: 97%

Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings

Doerksen

Hodík

et al. 2021

Chem. Rev.

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Ruthenium-catalyzed cycloadditions to form five-, six-, and seven-membered rings are summarized, including applications in natural product total synthesis. Content is organized by ring size and reaction type. Coverage is limited to processes that involve formation of at least one C–C bond. Processes that are stoichiometric in ruthenium or exploit ruthenium as a Lewis acid (without intervention of organometallic intermediates), ring formations that occur through dehydrogenative condensation-reduction, σ-bond activation-initiated annulations that do not result in net reduction of bond multiplicity, and photochemically promoted ruthenium-catalyzed cycloadditions are not covered.

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“…In a related study, Goswami and co-workers examined the same reaction under 'open-flask' conditions, using 2 mol% [Cp*RuCl(cod)] in ethanol at room temperature and a range of 2-[(hetero)arylseleno]pyridines were prepared in 82-90% yield (Scheme 79). 141 Unsymmetrical 1,6-diynes were also employed for this cycloaddition with selenocya- This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.…”

Section: Scheme 78mentioning

confidence: 99%

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Matton¹,

Huvelle²,

Haddad³

et al. 2021

Synthesis

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Metal-catalyzed [2+2+2] cycloaddition is a powerful tool that allows rapid construction of functionalized 6-membered carbo- and heterocycles in a single step through an atom-economical process with high functional group tolerance. The reaction is usually regio- and chemoselective although selectivity issues can still be challenging for intermolecular reactions involving the cross-[2+2+2] cycloaddition of two or three different alkynes and various strategies have been developed to attain high selectivities. Furthermore, enantioselective [2+2+2] cycloaddition is an efficient means to create central, axial, and planar chirality and a variety of chiral organometallic complexes can be used for asymmetric transition-metal-catalyzed inter- and intramolecular reactions. This review summarizes the recent advances in the field of [2+2+2] cycloaddition.1 Introduction2 Formation of Carbocycles2.1 Intermolecular Reactions2.1.1 Cyclotrimerization of Alkynes2.1.2 [2+2+2] Cycloaddition of Two Different Alkynes2.1.3 [2+2+2] Cycloaddition of Alkynes/Alkenes with Alkenes/Enamides2.2 Partially Intramolecular [2+2+2] Cycloaddition Reactions2.2.1 Rhodium-Catalyzed [2+2+2] Cycloaddition2.2.2 Molybdenum-Catalyzed [2+2+2] Cycloaddition2.2.3 Cobalt-Catalyzed [2+2+2] Cycloaddition2.2.4 Ruthenium-Catalyzed [2+2+2] Cycloaddition2.2.5 Other Metal-Catalyzed [2+2+2] Cycloaddition2.3 Totally Intramolecular [2+2+2] Cycloaddition Reactions3 Formation of Heterocycles3.1 Cycloaddition of Alkynes with Nitriles3.2 Cycloaddition of 1,6-Diynes with Cyanamides3.3 Cycloaddition of 1,6-Diynes with Selenocyanates3.4 Cycloaddition of Imines with Allenes or Alkenes3.5 Cycloaddition of (Thio)Cyanates and Isocyanates3.6 Cycloaddition of 1,3,5-Triazines with Allenes3.7 Cycloaddition of Aldehydes with Enynes or Allenes/Alkenes3.8 Totally Intramolecular [2+2+2] Cycloaddition Reactions4 Conclusion

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An Expeditious and Environmentally‐Benign Approach to 2‐Aryl/Heteroaryl Selenopyridines via Ruthenium Catalyzed [2+2+2] Cycloadditions

Cited by 14 publications

References 49 publications

Metal‐Free Synthesis of Aryl Selenocyanates and Selenaheterocycles with Elemental Selenium

Metal‐Free Synthesis of Aryl Selenocyanates and Selenaheterocycles with Elemental Selenium

Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

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