Catalytic Branching Cascades in Diversity Oriented Synthesis

Bansode, Avinash H.; Chimala, Prathyusha; Patil, Nitin T.

doi:10.1002/cctc.201600766

Cited by 13 publications

(6 citation statements)

References 75 publications

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“…In this regard, an overarching strategy, namely, "Divergent Synthesis", was conceptualized which mainly focused on the synthesis of diverse chemical compounds from essentially identical starting materials. 1−6 Emanating from this sole idea, various other similar concepts such as diversity-oriented synthesis (DOS), 7−12 diverted total synthesis (DTS), 13−16 and catalytic branching cascade, 17 etc. have been developed.…”

Section: Introduction: Divergent Gold Catalysis (Dgc)mentioning

confidence: 99%

“…An interesting approach in this regard would be the development of a synthetic strategy that can provide access to a wider chemical space from readily available starting materials. In this regard, an overarching strategy, namely, “Divergent Synthesis”, was conceptualized which mainly focused on the synthesis of diverse chemical compounds from essentially identical starting materials. − Emanating from this sole idea, various other similar concepts such as diversity-oriented synthesis (DOS), − diverted total synthesis (DTS), − and catalytic branching cascade, etc. have been developed.…”

Section: Introduction: Divergent Gold Catalysis (Dgc)mentioning

confidence: 99%

“…Despite the rapid increase in reports of this kind, the reviews documenting such examples have remained sporadic. ,,, As a result, most of the reports of this kind remain scattered in the literature, thereby hampering further development of this exciting field. Hence, owing to our continuous involvement in the field of gold catalysis, ,− we thought that it would be highly advantageous to bring all such reports under one umbrella, which perhaps served as a key motivation to present this comprehensive review by conceptualizing the idea of “Divergent Gold Catalysis (DGC)”.…”

Section: Introduction: Divergent Gold Catalysis (Dgc)mentioning

confidence: 99%

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Divergent Gold Catalysis: Unlocking Molecular Diversity through Catalyst Control

et al. 2021

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The catalyst-directed divergent synthesis, commonly termed as “divergent catalysis”, has emerged as a promising technique as it allows chartering of structurally distinct products from common substrates simply by modulating the catalyst system. In this regard, gold complexes emerged as powerful catalysts as they offer unique reactivity profiles as compared to various other transition metal catalysts, primarily due to their salient electronic and geometrical features. Owing to the tunable soft π-acidic nature, gold catalysts not only evolved as superior contenders for catalyzing the reactions of alkynes, alkenes, and allenes but also, more intriguingly, have been found to provide divergent reaction pathways over other π-acid catalysts such as Ag, Pt, Pd, Rh, Cu, In, Sc, Hg, Zn, etc. The recent past has witnessed a renaissance in such examples wherein, by choosing gold catalysts over other transition metal catalysts or by fine-tuning the ligands, counteranions or oxidation states of the gold catalyst itself, a complete reactivity switch was observed. However, reviews documenting such examples are sporadic; as a result, most of the reports of this kind remained scattered in the literature, thereby hampering further development of this burgeoning field. By conceptualizing the idea of “Divergent Gold Catalysis (DGC)”, this review aims to consolidate all such reports and provide a unified approach necessary to pave the way for further advancement of this exciting area. Based on the factors governing the divergence in product formation, an explicit classification of DGC has been provided. To gain a fundamental understanding of the divergence in observed reactivities and selectivities, the review is accompanied by mechanistic insights at appropriate places.

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Section: Introduction: Divergent Gold Catalysis (Dgc)mentioning

confidence: 99%

Section: Introduction: Divergent Gold Catalysis (Dgc)mentioning

confidence: 99%

Section: Introduction: Divergent Gold Catalysis (Dgc)mentioning

confidence: 99%

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Divergent Gold Catalysis: Unlocking Molecular Diversity through Catalyst Control

et al. 2021

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“…There have been reviews that focus on optimization studies and reactivities in gold catalysis; , however, a thematic review on the development of homogeneous sustainable gold catalysis at a ppm level has remained highly sporadic in the literature. , In light of our long-standing interest in the development of homogeneous gold catalysis, − herein, we would like to present a comprehensive perspective summarizing all the reports that employ catalyst loadings ≤ 0.1 mol %. A special emphasis on the roles of electronic and steric effects of ligands to achieve high turnover numbers (TONs) and turnover frequencies (TOFs) are given for a better understanding for the readers.…”

Section: Introductionmentioning

confidence: 99%

Ligand-Enabled Sustainable Gold Catalysis

Kumar

Patil

2022

ACS Sustainable Chem. Eng.

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Gold catalysis has emerged as an efficient tool in the field of synthetic organic chemistry. Despite the significant progress, the need for high catalyst loadings has mainly hampered its applicability in large-scale synthesis. Recent research has showcased the importance of ligand engineering to realize gold-catalyzed organic transformations at low catalyst loadings, at milder reactions conditions, and in greener solvents. In this perspective, we summarized the reports that clearly emphasize the crucial role of ligands in achieving the highly efficient gold-catalyzed organic transformations at low catalysts loadings (≤0.1 mol %) with high turnover numbers and turnover frequencies. This perspective also briefly discusses the challenges and future potential for the development of ppm-level gold catalysis.

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“…Powerful tools such as domino processes, currently recognized for their great ability to generate architectural complexity, , still remain less exploited in this research area. However, quite recently, such processes have revealed their high potential to generate molecular diversity starting from common substrates by ingeniously acting on the course of the concerned reaction sequences. , …”

Section: Introductionmentioning

confidence: 99%

Structure-Based Kinetic Control in a Domino Process: A Powerful Tool Toward Molecular Diversity in Chromone Series

et al. 2017

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Two successive original routes leading to two novel families of polyheterocycles starting from the versatile chromone-based Michael acceptors platform are reported herein. The major aspect of this work is the selective access to these frameworks by changing the course of the domino process involved in their formation. First, enaminochromanones were selectively accessed under uncommon kinetic control. In this study, we showed that the tuning of the selectivity toward the kinetic product could be achieved by key structural modifications of the different reaction partners involved in the domino process. Once selectivity was efficiently controlled, enaminochromanones were ultimately transformed into a more complex family of polyheterocycles containing the pyrrolo-oxazinone framework. Here, the modulation of the domino sequence toward these particularly scarce structures was enabled by a pivotal switch in reactivity induced by aryl-λ-iodanes.

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Catalytic Branching Cascades in Diversity Oriented Synthesis

Cited by 13 publications

References 75 publications

Divergent Gold Catalysis: Unlocking Molecular Diversity through Catalyst Control

Divergent Gold Catalysis: Unlocking Molecular Diversity through Catalyst Control

Ligand-Enabled Sustainable Gold Catalysis

Structure-Based Kinetic Control in a Domino Process: A Powerful Tool Toward Molecular Diversity in Chromone Series

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