A cascade process for the synthesis of ortho-formyl allyl aryl ethers and 2H-chromen-2-ol derivatives from arynes via trapping of o-quinone methide with an activated alkene

Sharma, Abhilash; Gogoi, Pranjal

doi:10.1039/c8ob02507j

Cited by 23 publications

(10 citation statements)

References 77 publications

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“…Moreover, Gogoi and co-workers developed two protocols using either 2-bromoacetophenones or activated alkenes as the electrophilic components in the reactions with o -quinone methide. When 2-bromoacetophenones 8-167 were employed, 2-aroyl benzofurans 8-155 were achieved in good to high yields via an O-alkylation on 8-145 to form 8-168 /annulation/aromatization process (Scheme a) .…”

Section: Multicomponent Reactions (Mcrs)mentioning

confidence: 86%

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

2021

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Arynes are among the most active organic intermediates and have found numerous applications in expeditious preparation of substituted arenes. In the past 20 years, chemists have witnessed a resurgence in aryne chemistry, which is mainly attributed by the extensive utilization of Kobayashi's method, a fluoride-induced removal of the TMS group with concomitant departure of its ortho OTf group on o-silylaryl triflates. Nowadays, o-silylaryl triflates are the most frequently employed aryne precursors. This review provides an overview of the history of Kobayashi's method, its methodological achievements, and its applications in the synthesis of natural products, bioactive molecules, and polycyclic aromatic hydrocarbons.

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Section: Multicomponent Reactions (Mcrs)mentioning

confidence: 86%

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

2021

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“…trapped o-quinone methides with sulfonyl chlorides 66 and allyl halides, 61 and in the presence of H 2 O, salicylaldehyde derivatives were generated. 67 Similar to carbonyl (C=O), insertion of aryne into S + -Oof sulfoxides proceeds via a formal [2+2] cycloadduct 54 (Scheme 20).…”

Section: Account Syn Lettmentioning

confidence: 99%

Aryne-Based Multicomponent Coupling Reactions

Ghorai¹,

Lee²

2020

Synlett

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Multicomponent reactions (MCRs) constitute a powerful synthetic tool to generate a large number of small molecules with high atom economy, which thus can efficiently expand the chemical space with molecular diversity and complexity. Aryne-based MCRs offer versatile possibilities to construct functionalized arenes and benzo-fused heterocycles. Because of their electrophilic nature, arynes couple with a broad range of nucleophiles. Thus, a variety of aryne-based MCRs have been developed, the representative of which are summarized in this account.1 Introduction2 Aryne-Based Multicomponent Reactions2.1 Trapping with Isocyanides2.2 Trapping with Imines2.3 Trapping with Amines2.4 Insertion into π-Bonds2.5 Trapping with Ethers and Thioethers2.6 Trapping with Carbanions2.7 Transition-Metal-Catalyzed Approaches3 Strategies Based on Hexadehydro Diels–Alder Reaction3.1 Dihalogenation3.2 Halohydroxylation and Haloacylation3.3 Amides and Imides3.4 Quinazolines3.5 Benzocyclobutene-1,2-diimines and 3H-Indole-3-imines3.6 Other MCRs of Arynes and Isocyanides4 Conclusion

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“…Additionally, Studer and his group designed an interesting cascade reaction for o -arylsulfinyl aryl vinyl ethers using aryne and aryl vinyl sulfoxides which proceeds via insertion of aryne into the S–O σ-bond and concomitant stereospecific S–O-vinyl migration. As a part of our research on the development of aryne methodologies, we have developed a new synthetic protocol for the direct synthesis of functionalized aryl sulfide via three-component reactions of aryne, DMSO, and activated alkyne (Scheme ).…”

mentioning

confidence: 88%

Three-Component Coupling Reactions of Aryne, DMSO, and Activated Alkyne: Stereoselective Synthesis of 2-[(o-Methylthio)aryloxy]-Substituted Dialkyl Maleates

et al. 2019

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A transition-metal-free coupling reaction of aryne, DMSO, and activated alkyne for the synthesis of 2-[(o-methylthio)aryloxy]-substituted dialkyl maleates is reported. This cascade process is associated with several bond cleavage as well as bond formation reactions in one pot. One of our synthesized maleates has been unambiguously established by single-crystal XRD studies. This methodology allows preparation of trisubstituted vinyl ethers with excellent stereospecificity.

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A cascade process for the synthesis of ortho-formyl allyl aryl ethers and 2H-chromen-2-ol derivatives from arynes via trapping of o-quinone methide with an activated alkene

Abstract: A transition-metal free synthetic strategy for the direct synthesis of ortho-formyl substituted allyl aryl ethers and 2H-chromen-2-ol derivatives via a cascade three-component coupling of arynes, activated alkene and N,N-dimethylformamide.

Cited by 23 publications

References 77 publications

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

Aryne-Based Multicomponent Coupling Reactions

Three-Component Coupling Reactions of Aryne, DMSO, and Activated Alkyne: Stereoselective Synthesis of 2-[(o-Methylthio)aryloxy]-Substituted Dialkyl Maleates

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