Last Decade of Unconventional Methodologies for the Synthesis of Substituted Benzofurans
Abstract
:1. Introduction
2. Ring Generation via Intra-Molecular Cyclization
2.1. C7a–O Bond Formation: (Route a)
2.1.1. From o-Halophenylacetylenes
2.1.2. From o-Halo-Benzylketones
2.2. O–C2 Bond Formation: (Route b)
2.2.1. Via C-H Activation of o-Alkenylphenols
2.2.2. From o-Alkynylphenols
2.2.3. From o-Gem-Dibromoalkenyl Phenols
2.2.4. From o-Allylphenols
2.2.5. From o-Hydroxybenzyl Ketones
2.2.6. From o-(Cyanomethyl) Phenols
2.2.7. From 1-(2-hydroxyphenyl) Propargyl Alcohol Derivatives
2.3. C2–C3 Bond Formation: (Route c)
2.3.1. From o-(Alkoxy)Phenyl Arylketones
2.3.2. From o-Alkynylphenyl benzyl (or Allyl)Ethers
2.3.3. From o-Alkynylphenyl Vinylethers
2.3.4. From o-Triazole-Phenyl Benzylethers
2.4. C3–C3a Bond Formation: (Route d)
2.4.1. Via Friedel–Crafts Acylation
2.4.2. Via [Ru(II)] C-H Insertion of N-Sulfonyl-1,2,3-Triazole Derivatives
2.4.3. Via [Pd(0)] C–H Insertion
2.4.4. Via Radical Cyclization of o-Iodophenyl Allenyl Ethers
3. Ring Generation via Intermolecular Cyclization
3.1. C7a–O and C3–C3a Bond Formation: (Route a + d)
3.1.1. Via o-C-H alkylation/Decarboxylation
3.1.2. Via Propargyl Claisen Rearrangement/Cycloaddition
3.1.3. Via Addition of Zinc-Enolate to Methines
3.2. O–C2 and C2–C3 Bond Formation: (Route b + c)
3.2.1. Via Transition-Metal-Free Catalyzed Approaches: p-Quinone Methides
3.2.2. Via transition-Metal-Free Catalyzed Approaches: o-Quinone Methides
3.2.3. Via Transition-Metal-Free Catalyzed Approaches: o-Hydroxyphenone or Salicylaldehydes
3.2.4. Transition-Metal-Catalyzed Approaches: [Rh(II)] Catalyzed Addition of N-Sulfonyl-1,2,3-Triazole
3.2.5. Transition–Metal Catalyzed Approaches: [Cu(I)]-Catalyzed Addition to o-Hydroxybenzophenones/Salicylaldehydes
3.2.6. Miscellaneous
3.3. O–C2 and C3–C3a Bond Formation: (Route b + d)
3.3.1. From o-Halophenols and Terminal Alkynes
3.3.2. From o-Halophenols and Internal Alkynes
3.3.3. From o-Halophenols and Allenes
3.3.4. From Phenols: O-aryloxime/[3,3]-Sigmatropic Rearrangement/Cyclization
3.3.5. Via Transition-Metal-Catalyzed Annulation of N-Aryloxyacetamides and Propargyl Alcohols
3.3.6. Metal-Free [3 + 2] Annulation of Phenols with Acetylenes
3.3.7. [Pd]-Catalyzed [3 + 2] Annulation of Phenols with Internal Alkynes
3.3.8. Via Interrupted Pummerer Reaction/[3,3] Sigmatropic Rearrangement/Cyclization
3.3.9. Via Fries-type O-C Rearrangement/Michael Addition of Phenols
3.3.10. Via [Ru]-Catalyzed C–H Alkylation of Phenols with 1,2-Diols
3.3.11. Via [Rh]-Catalyzed Carbene Insertion with Phenols/Salicylaldehydes
3.3.12. Via Michael Addition/Cyclization of Nucleophiles on Benzoquinones
3.3.13. Via FeCl3-Catalyzed Allenic Claisen Rearrangement/ Dehydrogenative Cyclization
4. Benzoannulation
5. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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Chiummiento, L.; D’Orsi, R.; Funicello, M.; Lupattelli, P. Last Decade of Unconventional Methodologies for the Synthesis of Substituted Benzofurans. Molecules 2020, 25, 2327. https://doi.org/10.3390/molecules25102327
Chiummiento L, D’Orsi R, Funicello M, Lupattelli P. Last Decade of Unconventional Methodologies for the Synthesis of Substituted Benzofurans. Molecules. 2020; 25(10):2327. https://doi.org/10.3390/molecules25102327
Chicago/Turabian StyleChiummiento, Lucia, Rosarita D’Orsi, Maria Funicello, and Paolo Lupattelli. 2020. "Last Decade of Unconventional Methodologies for the Synthesis of Substituted Benzofurans" Molecules 25, no. 10: 2327. https://doi.org/10.3390/molecules25102327