Condition‐Controlled Selective Synthesis of CF₃‐Chromene and CF₃‐Benzofuran from N‐Phenoxyacetamide and CF₃‐Ynone

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

Comprehensive Summary Presented herein is a condition‐controlled selective synthesis of CF 3 ‐chromene and ‐benzofuran based on the reaction N ‐phenoxyacetamide ‐ynone. When carried out in MeOH under catalysis Rh(III), formed via C—H metalation‐initiated alkenylation, acetamide group migration intramolecular oxo ‐nucleophilic addition. On other hand, when run DMSO promotion CsOAc, generated aza ‐Michael addition‐initiated [3,3]‐σ rearrangement, addition water elimination. To our knowledge, this first report construction chromene or benzofuran scaffold along with introduction unit from same starting materials. The methodology was scalable products could be readily transformed into valuable products. Moreover, thus obtained possess decent anticancer activity.

Language: Английский

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Cobalt(III)-Catalyzed Intermolecular Carboamination of Propiolates and Bicyclic Alkenes via Non-Annulative Redox-Neutral Coupling

Organic Letters, Journal Year: 2019, Volume and Issue: 21(15), P. 5884 - 5888

Published: July 24, 2019

A cobalt(III)-catalyzed, redox-neutral, intermolecular carboamination of propiolates and bicyclic alkenes was developed. This non-annulative coupling strategy features atom economy, high regioselectivity, good yields, functional groups tolerance. Such a reaction applied to modified phenols from the corresponding under mild conditions.

Language: Английский

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Directing-Group-Assisted Transition-Metal-Catalyzed Direct C–H Oxidative Annulation of Arenes with Alkynes for Facile Construction of Various Oxygen Heterocycles

Synthesis, Journal Year: 2020, Volume and Issue: 52(07), P. 993 - 1006

Published: Feb. 10, 2020

The most recent advances in the construction of oxygen heterocycles by directing-group-assisted transition-metal-catalyzed direct oxidative annulation arenes with diverse alkynes are summarized this review. More than 140 research papers and many closely related reviews referenced paper. Nine different frameworks discussed. Several traditional transition-metal catalysts as well some classical non-noble metals utilized to promote annulation. Three plausible controlling models disclosed clarify excellent regioselectivity outcomes achieved case unsymmetrical alkyne substrates. 1 Introduction 2 Coumarins 3 I socoumarins Their Analogues 4 2-Pyrones 5 Chromones Chroman-4-ones 6 Chromenes Isochromenes 7 Fused Polycyclic Oxygen Heteroaromatics 8 Benzofurans, Dihydrobenzofurans, Furans 9 Phthalides Benzofuranones 10 Benzoxepines 11 Conclusion

Language: Английский

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Rh(III)-Catalyzed Regioselective Annulations of 3-Arylisoxazolones and 3-Aryl-1,4,2-dioxazol-5-ones with Propargyl Alcohols: Access to 4-Arylisoquinolines and 4-Arylisoquinolones

Organic Letters, Journal Year: 2021, Volume and Issue: 23(15), P. 5952 - 5957

Published: July 29, 2021

The Rh(III)-catalyzed dual directing group assisted C–H activation/annulation of 3-arylisoxazolones with propargyl alcohols has been developed, which expands the application scope isoxazolones in organic synthesis. This protocol also worked well 3-aryl-1,4,2-dioxazol-5-ones to produce synthetically and biologically important 4-arylisoquinolones.

Language: Английский

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Recyclable rhodium-catalyzed C–H activation/[4 + 2] annulation with unconventional regioselectivity at ambient temperature: experimental development and mechanistic insight

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(18), P. 7012 - 7021

Published: Jan. 1, 2022

A robust and convenient rhodium-catalyzed unconventionally regioselective C–H activation/[4 + 2] annulation for the synthesis of isoquinolones which are prevalent in natural products pharmaceuticals was developed.

Language: Английский

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Synthesis of 2-aminobenzofurans via base-mediated [3 + 2] annulation of N-phenoxy amides with gem-difluoroalkenes

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(16), P. 4452 - 4458

Published: Jan. 1, 2021

Efficient metal-free [3 + 2] annulation of N-phenoxy amides with gem-difluoroalkenes has been realized for the assembly 2-aminobenzofuran derivatives potent cytotoxicity against cancer cell lines and application potential DELs.

Language: Английский

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Kinetic Resolution of Azaarylethynyl Tertiary Alcohols by Chiral Brønsted Acid Catalysed Phosphine‐Mediated Deoxygenation

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 62(4)

Published: Nov. 22, 2022

A chiral Brønsted acid catalysed phosphine-mediated deoxygenation protocol is reported. This metal-free method provides a precise kinetic resolution platform for azaarylethynyl tertiary alcohols, which are broad category of biologically and synthetically important azaarene derivatives. In addition to providing an efficient the first asymmetric preparation these strategy facilitates construction azaaryl-functionalized allenes with good excellent enantioselectivities. The high selectivity factors (s up 235), substrate scope, ability convert azaaryl compounds into both alcohols robustly underscore efficiency promising utility this method. practicability further validated by successful synthesis deuterated ee values substantial incorporation deuterium using inexpensive D2 O as source.

Language: Английский

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Cascade Alkenylation/Intramolecular Friedel–Crafts Alkylation: High Selectivity at the C7-Position of BINOL

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 6108 - 6119

Published: April 3, 2023

An efficient and straightforward approach for the synthesis of C7 site-selective BINOL derivatives has been achieved via cost-effective Co(III)-catalyzed C-H cascade alkenylation/intramolecular Friedel-Crafts alkylation units propargyl cycloalkanols. Under advantage pyrazole directing group, protocol allows rapid various BINOL-tethered spiro[cyclobutane-1,1'-indenes].

Language: Английский

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Rhodium-catalyzed regioselective C–H activation/Lossen rearrangement/annulation for the green synthesis of trisubstituted 2-pyridones

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(12), P. 3000 - 3009

Published: Jan. 1, 2023

A green and novel approach for the synthesis of 2-pyridone derivatives by a rhodium-catalyzed C–H activation/Lossen rearrangement acrylamides propargyl alcohols is reported.

Language: Английский

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Rh(III)‐Catalyzed Redox‐Neutral [4+2] Annulation for Direct Assembly of 3‐Acyl Isoquinolin‐1(2H)‐ones as Potent Antitumor Agents

ChemPlusChem, Journal Year: 2019, Volume and Issue: 85(3), P. 405 - 410

Published: Nov. 15, 2019

Abstract By virtue of an efficient rhodium(III)‐catalyzed redox‐neutral C−H activation/ring‐opening a strained ring/[4+2] annulation cascade N ‐methoxybenzamides with propargyl cycloalkanols, diverse 3‐acyl isoquinolin‐1(2 H )‐ones were directly obtained in good yields and excellent functional group compatibility. Additionally, their antitumor activities against various human cancer cells including HepG2, A549, MCF‐7 SH‐SY5Y evaluated the action mechanism selected compound was also investigated vitro . The results revealed that these products possessed potent efficacy, by inhibiting proliferation inducing apoptosis time‐dependent dose‐dependent manner, suggesting such compounds can serve as promising candidates for anti lung drug discovery.

Language: Английский

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