MeOTf-induced carboannulation of arylnitriles and aromatic alkynes: a new metal-free strategy to construct indenones

Yan, Xiaoyu; Zou, Siyu; Zhao, Peng; Xi, Chanjuan

doi:10.1039/c4cc00088a

Cited by 62 publications

(44 citation statements)

References 35 publications

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“…However, electrophilicity of N -alkylated nitriliums has rarely been used in further reactions until recently. In 2014, our group [47] reported MeOTf-induced carboannulation of arylnitriles and aromatic alkynes to construct indenones 1 (scheme 2). Triflate 3 was isolated when 5-decyne was used indicating I-1 might be an intermediate in this reaction.…”

Section: Rotf-induced Annulation Of Nitrogen-containing Substrates Wimentioning

confidence: 99%

ROTf-induced annulation of heteroatom reagents and unsaturated substrates leading to cyclic compounds

Zou

Wang

2018

R. Soc. open sci.

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The development of metal-free organic reactions is one of the hotspots in the synthesis of cyclic compounds. ROTf (alkyl trifluoromethanesulfonates), due to their good electrophilicity, are powerful alkylating reagents at heteroatoms such as nitrogen, oxygen, sulfur and phosphorus to induce an electrophilic centre for carbon–carbon or carbon–heteroatom bond formation. Inspired by this chemistry, a variety of research concentrating on heterocycles synthesis has been carried out. In this review, we mainly summarize the ROTf-induced annulation of heteroatom reagents such as nitriles, carbodiimides, azobenzenes, isothiocyanates, aldehydes, isocyanates and phosphaalkene with themselves or alkynes to afford cyclic compounds.

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Section: Rotf-induced Annulation Of Nitrogen-containing Substrates Wimentioning

confidence: 99%

ROTf-induced annulation of heteroatom reagents and unsaturated substrates leading to cyclic compounds

Zou

Wang

2018

R. Soc. open sci.

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“…[18] Therefore,t here is ac ontinued strong demand for developing efficient and selective synthetic approaches to access these valuable scaffolds.T raditional synthetic methods lack generality and have limited substrate scope. [19] In recent years,t ransition-metal-catalyzed cyclization with internal alkynes through chelation-assisted C À Ha ctivation [20] or multiple cross-couplings [21] has been recognized as an increasingly viable tool for the preparation of indenones (Scheme 1b). Despite these major advances,t he poor regioselectivity using unsymmetrical alkynes as the coupling partners still represents ad rawback.…”

Section: Introductionmentioning

confidence: 99%

Rhenium‐Catalyzed Arylation–Acyl Cyclization between Enol Lactones and Organomagnesium Halides: Facile Synthesis of Indenones

Cheng

et al. 2021

Angew Chem Int Ed

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As et of rhenium-catalyzeda rylation-acyl cyclizations between (hetero)arylmagnesium halides and enol lactones through ac ascade C(sp 2 )ÀC(sp 2 )/C(sp 2 )ÀC(sp 2 )b ond formation under mild reaction conditions has been developed. Indeed, aw ide range of functional groups on both organomagnesium halides and enol lactones is well tolerated by the simple rhenium catalysis,t hus furnishing polyfunctionalized indenones in one-pot fashion and with complete control of the regioselectivity.M oreover,t his approacha lso provides as traightforwards ynthetic route to neolignan and (iso)pauciflorol F. Mechanistic studies demonstrated that the reaction involves asequence of syn-carborhenation and intramolecular nucleophilic addition.

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“…As a result, a considerable number of methods for their synthesis have been developed. [6] Transition-metal-catalyzed domino cyclization of ortho-carbonylated aryl halides and alkynes is one of the most straightforward methods to construct indenone scaffolds (Route a, Scheme 1 a, top). [7] Rhodium-catalyzed direct C À H bond annulation reaction for the synthesis of indenones has also been reported (Route b, Scheme 1 a, top).…”

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Synthesis of Indanones and Spiroindanones by Diastereoselective Annulation Based on a Hydrogen Autotransfer Strategy

et al. 2021

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An unprecedented nickel-catalyzed domino reductive cyclization of alkynes and o-bromoaryl aldehydes is described. The reaction features broad substrate scope and is tolerant of a variety of functional groups, providing straightforward access to biologically significant indanones and spiroindanone pyrrolidine derivatives in good yields with excellent regio-and diastereoselectivity. Preliminary mechanistic studies have shown that indanones are formed by the cyclization of o-bromoaryl aldehydes and alkynes to form indenol intermediates, followed by hydrogen autotransfer.

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MeOTf-induced carboannulation of arylnitriles and aromatic alkynes: a new metal-free strategy to construct indenones

Abstract: MeOTf-induced carboannulation of arylnitriles and aromatic alkynes for synthesis of indenones under metal-free conditions has been described. When ortho-substituted benzonitriles were used, indeno[1,2-c]isoquinolines were formed.

Cited by 62 publications

References 35 publications

ROTf-induced annulation of heteroatom reagents and unsaturated substrates leading to cyclic compounds

ROTf-induced annulation of heteroatom reagents and unsaturated substrates leading to cyclic compounds

Rhenium‐Catalyzed Arylation–Acyl Cyclization between Enol Lactones and Organomagnesium Halides: Facile Synthesis of Indenones

Synthesis of Indanones and Spiroindanones by Diastereoselective Annulation Based on a Hydrogen Autotransfer Strategy

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