Organocatalytic Asymmetric Dearomative Spirocyclization/Oxa-Michael Addition Sequence: Synthesis of Polycyclic Tetralones

Organic Letters, Год журнала: 2024, Номер 26(15), С. 3179 - 3183

Опубликована: Апрель 3, 2024

Herein, an organocatalytic asymmetric dearomative spirocyclization/oxa-Michael addition sequence with a newly designed substrate having two naphthol motifs has been developed. The reaction proceeds through in situ chiral vinylidene ortho-quinone methide (VQM) intermediate formation, spirocyclization of naphthol, and oxa-Michael reaction. densely functionalized tetralone products were formed high yields diastereo- enantioselectivities.

Язык: Английский

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Silver‐Free C−H Activation: Strategic Approaches towards Realizing the Full Potential of C−H Activation in Sustainable Organic Synthesis

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(48)

Опубликована: Сен. 5, 2022

The activation of carbon-hydrogen bonds is considered as one the most attractive techniques in synthetic organic chemistry because it bears potential to shorten routes well produce complementary product scopes compared traditional strategies. However, many current methods employ silver salts additives, leading stoichiometric metal waste and thereby preventing full C-H be exploited. Therefore, development silver-free protocols has recently received increasing attention. Mechanistically, can serve various roles thus, avoiding use requires different approaches based on role serves a given process. In this Review, we present comparison silver-based methods. Focusing strategic develop activation, provide reader with means sustainable for activation.

Язык: Английский

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Electrochemical Palladium‐Catalyzed Oxidative Carbonylation‐Cyclization of Enallenols

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(49)

Опубликована: Окт. 12, 2022

Herein, we report an electrochemical oxidative palladium-catalyzed carbonylation-carbocyclization of enallenols to afford γ-lactones and spirolactones, which proceeds with excellent chemoselectivity. Interestingly, electrocatalysis was found have accelerating effect on the rate tandem process, leading a more efficient reaction than that under chemical redox conditions.

Язык: Английский

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Review of electrochemical transition‐metal‐catalyzed C−H functionalization reactions

ChemistrySelect, Год журнала: 2023, Номер 8(11)

Опубликована: Март 14, 2023

Abstract The combination of organometallic C−H activation and electro‐catalysis has emerged as a potent synthetic technique for various molecular scaffolds since it avoids the use harmful expensive chemical oxidants in stoichiometric amounts. Moreover, pre‐functionalization substrates is not required newer ways to perform metal‐catalyzed reactions are possible. Here, we have discussed eletrochemically driven acyloxylation, acetoxylation, oxygenation, acylation, amination, alkylation, halogenation, olefinations C−H/N−H annulation using transition‐metal‐catalyst such Ru, Rh, Pd, Co, Ni, Ir, Cu, Mn Au by anodic oxidation, followed reductive elimination form corresponding C−O, C−C, C−N C−X (X=Cl, Br, S etc.) bonds. This review covers recent developments transition‐metal‐catalyzed electrochemical from 2007 until 2022.

Язык: Английский

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Pd-catalyzed regioselective rollover dual C–H annulation cascade: facile approach to phenanthrene derivatives

Chemical Communications, Год журнала: 2023, Номер 59(64), С. 9714 - 9717

Опубликована: Янв. 1, 2023

A Pd-catalyzed rollover cascade dual C–H annulation of aryl phenols with alkynols for producing phenanthrene scaffolds in a regioselective manner was developed. Necessary control, KIE and deuterium experiments were conducted to determine the reaction mechanism.

Язык: Английский

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