Diversity-Oriented Synthesis of Indole-Fused Polycyclic Scaffolds via Rhodium-Catalyzed NH-Indole-Directed C–H Coupling of 2-Phenyl-1H-indoles with Propargylic Alcohol Derivatives

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(8), С. 5589 - 5605

Опубликована: Апрель 5, 2024

Diversity-oriented synthesis strategy for the efficient assembly of indole-fused polycyclic scaffolds via rhodium-catalyzed NH-indole-directed C–H coupling with propargylic alcohol derivatives in a regioselective manner was developed. Five 2-phenyl-1H-indole-embedded core skeletons were synthesized. In particular, three different exo-olefin-containing polycycles realized, which may be manipulated further chemistry.

Язык: Английский

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Conjugated Olefin Enabled Rollover Cyclometallation of Distant C‐H Bonds: Regioselective Annulation of o‐Alkenyl Phenols with Alkynes

Chemistry - A European Journal, Год журнала: 2023, Номер 29(70)

Опубликована: Окт. 11, 2023

Although challenging, the distant C-H functionalization with precision is quite rewarding and has long been intriguing. Tailoring an appropriate template accomplishes job but prerequisite sets limitation. We herein unveil our discovery of annulation alkynes on to two (from directing group) bonds through rollover cyclometallation assisted by conjugated C=C bond. The follows a concomitant cyclization rare triple functionalization. totally regioselective array unsymmetrical alkynes, taking leverage extended conjugation or tertiary hydroxyl co-ordination. mechanism supported control experiments, KIE & labelling studies Mass spectrometry.

Язык: Английский

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Pd‐Catalyzed Vicinal Intermolecular Annulations of Iodoarenes, Indoles, and Carbazoles with Enynes

Chemistry - A European Journal, Год журнала: 2023, Номер 30(7)

Опубликована: Ноя. 6, 2023

Reaching the formidable C-H corners has been one of top priorities organic chemists in recent past. This prompted us to disclose herein a vicinal annulation 2-iodo benzoates, indoles, and carbazoles with N-embedded 1,6-enynes through 7-/8-membered palladacycles. The relay does not require assistance any directing group, leading multicyclic scaffolds, which are readily diversified an array adducts (with new functional tethers and/or three contiguous stereocenters), we showcase rare benzylic mono-oxygenation.

Язык: Английский

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Oxidative Cyclization of Oximes with Propargyl Alcohols toward Functionalized Isoquinoline N‐Oxides Synthesis

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 13(1)

Опубликована: Ноя. 29, 2023

Abstract An efficient and regioselective synthesis of various functionalized isoquinoline N ‐oxides has been realized by Rh(III)‐catalyzed oxidative annulation aryl oximes with tertiary propargyl alcohols. The current protocol features readily available starting materials, mild reaction conditions, broad substrate scope wide functional group tolerance.

Язык: Английский

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Propargyl Alcohols as Bifunctional Reagents for Divergent Annulations of Biphenylamines via Dual C−H Functionalization/Dual Oxidative Cyclization

Angewandte Chemie, Год журнала: 2022, Номер 135(12)

Опубликована: Дек. 30, 2022

Abstract The C−H functionalization strategy provides access to valuable molecules that previously required convoluted synthetic attempts. Dual unsymmetrical functionalization, with a single bifunctional reagent, is an effective tactic. Propargyl alcohols (PAs), despite containing reactive C≡C bond, have not been explored as building blocks via oxidative cleavage. Annulations activation are versatile and synthetically attractive strategy. We disclose PA new reagent for dual of biphenylamine regioselectively annulated outcomes. On tuning the conditions, annulation bifurcated towards unusual cyclization. This method accommodates wide range PAs showcases late‐stage diversification some natural products.

Язык: Английский

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Rh(iii)-catalyzed (5 + 2)-cycloaddition reactions of ortho-hydroxyethyl phenols with internal alkynes: efficient synthesis of benzoxepines

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(12), С. 2516 - 2523

Опубликована: Янв. 1, 2023

An unprecedented (5 + 2)-cycloaddition reaction of ortho-hydroxyethyl phenol and internal alkyne was developed. This Rh(III)-catalyzed provided benzoxepine derivatives which have very high biological significance. A wide range phenols alkynes were studied to provide the benzoxepines in yields.

Язык: Английский

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Rapid Alkynylation of Ketones in Air: A Base Mediated, Metal Catalyst and Solvent‐Free Approach

ChemistrySelect, Год журнала: 2023, Номер 8(28)

Опубликована: Июль 24, 2023

Abstract The straightforward grinding of terminal alkynes and ketones/isatin in the presence base, without use any catalyst or a solvent, appears to be viable method for producing tertiary propargylic alcohols. This energy time‐efficient rapid reaction opens up greener pathway synthesis alcohols with moderate good yields as compared contemporary methodologies.

Язык: Английский

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