Au-Catalyzed Synthesis and Functionalization of Heterocycles

doi:10.1007/978-3-319-35144-5

Cited by 19 publications

(1 citation statement)

References 37 publications

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“…Gold (I or III) complexes are the most effective catalysts for electrophilic activation of alkynes, with a wide field of synthetic applications; few other less-acidic late transition metals, such as Pt (II) or Ag(I), can be used as an alternative. The large tolerance of gold catalysis toward heteroatoms make gold catalysis a powerful and useful tool for the synthesis of functionalized molecular scaffolds, including heterocyclic cores [74].…”

Section: Methods Using Gold-or Silver-catalyzed Reactionsmentioning

confidence: 99%

Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

et al. 2020

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Medium-sized heterocycles (with 8 to 11 atoms) constitute important structural components of several biologically active natural compounds and represent promising scaffolds in medicinal chemistry. However, they are under-represented in the screening of chemical libraries as a consequence of being difficult to access. In particular, methods involving intramolecular bond formation are challenging due to unfavorable enthalpic and entropic factors, such as transannular interactions and conformational constraints. The present review focuses on the synthesis of medium-sized heterocycles by transition-metal-catalyzed intramolecular cyclization, which despite its drawbacks remains a straightforward and attractive synthesis strategy. The obtained heterocycles differ in their nature, number of heteroatoms, and ring size. The methods are classified according to the metal used (palladium, copper, gold, silver), then subdivided according to the type of bond formed, namely carbon–carbon or carbon–heteroatom.

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Section: Methods Using Gold-or Silver-catalyzed Reactionsmentioning

confidence: 99%

Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

et al. 2020

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Gold‐Catalyzed C(sp ² )H Functionalization under Au(I)/Au(III) Catalysis

Urvashi¹,

Singh²,

Patil³

2022

Handbook of CH-Functionalization

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Among the newer approaches to transition metal‐catalyzed CH functionalization, Au(I)/Au(III) catalysis has emerged as a powerful synthetic tool for the construction of carbon–carbon and carbon–heteroatom bonds. The orthogonal reactivity pattern of gold catalysts as compared to other transition metal catalysts provides an excellent opportunity for the development of new modes of CH functionalization. The rapid enhancement in the field of gold‐catalyzed CH functionalization is complemented by the development of several strategies for achieving the typically arduous Au(I)/Au(III) redox cycle. This article documents all the examples of C(sp 2 )H functionalization under Au(I)/Au(III) catalysis reported so far.

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Gold‐Catalyzed Arylative Cope Rearrangement

Paroi,

Pegu,

Mane

et al. 2024

Angewandte Chemie

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Cope rearrangements have garnered significant attention owing to their ability to undergo structural reorganization in stereoselective manner. While substantial advances have been achieved over decades, these rearrangements remained applicable exclusively to parent 1,5‐hexadienes. Herein, we disclose the gold‐catalyzed arylative Cope rearrangement of 1,6‐heptadienes via a cyclization‐induced [3,3]‐rearrangement employing ligand‐enabled gold redox catalysis. Detailed mechanistic investigations including several control experiments, cross‐over experiment, HRMS analysis, 31P NMR and DFT studies have been performed to underpin the mechanism.

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Au-Catalyzed Synthesis and Functionalization of Heterocycles

Cited by 19 publications

References 37 publications

Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

Gold‐Catalyzed C(sp ² )H Functionalization under Au(I)/Au(III) Catalysis

Gold‐Catalyzed Arylative Cope Rearrangement

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Au-Catalyzed Synthesis and Functionalization of Heterocycles

Cited by 19 publications

References 37 publications

Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

Gold‐Catalyzed C(sp 2 )H Functionalization under Au(I)/Au(III) Catalysis

Gold‐Catalyzed Arylative Cope Rearrangement

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Gold‐Catalyzed C(sp ² )H Functionalization under Au(I)/Au(III) Catalysis