Weak‐Chelation Assisted Regioselective Indole C(4)‐Alkynylation via Six‐Membered Cobaltacycle Intermediate

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(6), С. 1341 - 1347

Опубликована: Янв. 13, 2024

Abstract Herein a regioselective indole C4‐alkynylation has been uncovered utilizing an earth‐abundant cobalt(III)‐catalyst. For this process, (bromoethynyl)benzene was used as alkynylating agent. Also, after screening various amide‐protected chelating groups we found dimethyl‐amide is optimal for the in‐situ generation of cobaltacycle intermediate. The six‐membered intermediate detected through high‐resolution mass spectrometry HRMS, which key conversion. Further, mechanistic studies were performed such KIE experiments, and reactions with radical scavengers, based on results plausible mechanism proposed. Moreover, to show application methodology, product oxidized diketone, monoketone, alkene, alkane further derivatized tricycle derivative, core structure many natural products.

Язык: Английский

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Co(III)-Catalyzed Regioselective Benzannulation of Substituted Pyridones with 1,6-Diynes via Dual C-H Bond Activation

Chemical Communications, Год журнала: 2024, Номер 60(63), С. 8296 - 8299

Опубликована: Янв. 1, 2024

A Co(III)-catalyzed site-selective C5 and C6 benzannulation of substituted pyridones with 1,6-diynes

Язык: Английский

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Pd-Catalyzed Selective Arylative Cascade Cyclization of 1,6-Diynes and Dibenzoxaborins for Fused Naphthalene Derivatives

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 10, 2025

A palladium-catalyzed new mode of cascade arylative cyclization 1,6-diynes is disclosed using dibenzoxaborin as an arylating agent featuring transmetalation and selective migratory insertion the key steps. This process enables efficient construction polysubstituted fused naphthalene skeletons via formation three C-C bonds through dual regioselectivity in both arylation well C-H functionalization. Some control experiments kinetic isotope effect (KIE) studies were conducted to elucidate reaction mechanism, some product diversifications achieved showcase synthetic potential.

Язык: Английский

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Electrochemical α‐Functionalization of N‐Aryl‐Activated Tertiary Amines

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(17), С. 3653 - 3663

Опубликована: Июнь 27, 2024

Abstract Numerous appropriately substituted pyridyl or phenyl groups serve as a particularly advantageous activation motif for the electrochemical oxidation of amines. Such enable general, mild method α‐functionalization tertiary amines across numerous activating and amine scaffolds. Notably, accommodates an unprecedented range nucleophile classes, allowing introduction diverse functional to readily prepared substrates. The utility this is then demonstrated through applications unsymmetrical bisfunctionalization, site‐selective functionalization N ‐pyridyl vs. other activated amines, formal synthesis ivosidenib diversification FDA‐approved drugs natural product

Язык: Английский

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Ir(III)-Catalyzed Tandem Annulation of Aromatic Amides with 1,6-Diynes via Dual C–H Bond Activation

Organic Letters, Год журнала: 2024, Номер 26(37), С. 7809 - 7816

Опубликована: Сен. 10, 2024

An Ir(III)-catalyzed annulation of aryl amides with 1,6-diynes

Язык: Английский

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