One-pot strategy: A highly economical tool in organic synthesis and medicinal chemistry

Yadav, Ram Naresh; Srivastava, Ashok; Banik, Bimal K.

doi:10.1016/b978-0-12-817592-7.00010-1

Cited by 10 publications

(8 citation statements)

References 183 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Noteworthy, the execution of multicatalytic multistep synthesis in a one-pot fashion, without or with limited intermediary workup, proved enabling and highly advantageous from the efficiency standpoint. 15,16 However, the development of such protocols with multiple transition-metal-catalyzed reactions operating in one vessel remains challenging. 17 The prospective cross-reactivity is likely to hinder the required activity.…”

mentioning

confidence: 97%

Multicatalytic Approach to One-Pot Stereoselective Synthesis of Secondary Benzylic Alcohols

et al. 2021

View full text Add to dashboard Cite

One-pot multi-step procedures bear the potential to rapidly build up molecular complexity while avoiding the wasteful and costly isolations and purifications of consecutive intermediates. Here we report multi-catalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Because each transformation of the sequence is executed by an independent catalyst, without any catalytic cross-reactivity, allylic alcohols bearing a prochiral double bond can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er and >20:1 dr). Overall, with the aid of up to four catalysts operating in a single vessel, the protocols directly convert simple starting materials into a range of value-added products with high stereocontrol and excellent material efficiency, demonstrating both the efficacy and the advantages of the one-pot synthesis employing multiple transition-metal catalysts.

show abstract

mentioning

confidence: 97%

Multicatalytic Approach to One-Pot Stereoselective Synthesis of Secondary Benzylic Alcohols

et al. 2021

View full text Add to dashboard Cite

show abstract

“…However, the field continues evolving in complexity to further increase its potential. [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] Recently, there has been growing interest in developing multi-catalytic systems, which are inspired by the complexity of catalytic reactions occurring in nature. 20,21 Such efforts are further driven by remarkable characteristics of biosynthesis, that is, excellent selectivity, high yields, and material efficiency when producing complex molecules directly without any isolation of intermediates.…”

Section: Introductionmentioning

confidence: 99%

“…Catalytic transformations are typically constrained to one catalyst enabling a single reaction. However, the field continues evolving in complexity to further increase its potential. − Recently, there has been growing interest in developing multicatalytic systems, which are inspired by the complexity of catalytic reactions occurring in nature. , Such efforts are further driven by remarkable characteristics of biosynthesis, that is, excellent selectivity, high yields, and material efficiency when producing complex molecules directly without any isolation of intermediates. However, to develop such multicatalytic systems, major challenges need to be addressed, including incompatibility between multiple catalysts or reagents, precise ordering of all individual processes, and operation of all reactions under a single set of conditions.…”

Section: Introductionmentioning

confidence: 99%

Challenges and Opportunities in Multicatalysis

et al. 2021

View full text Add to dashboard Cite

Multi-catalysis is an emerging field targeting the development of efficient catalytic transformations to quickly convert relatively simple starting materials into more complex valueadded products. Within multi-catalytic processes either multiple catalysts execute single reactions or precise sequences of multiple catalytic reactions occur in a 'one-pot' fashion. Attractively, multi-catalytic protocols not only enable transformations that are inaccessible through classic approaches, but also are able to significantly reduce the time, waste, and cost of the synthetic processes, making organic synthesis more resources efficient. In this Perspective article, we review different strategies in multi-catalysis that bring distinct challenges and opportunities. We divide this overarching field into three main categories: cooperative, domino, and relay catalysis. Each category is described along with representative examples to highlight its features. Special emphasis is dedicated to relay catalysis, which is further discussed in its sub-categories. Lastly, we provide an analysis of systems that incorporate higher levels of complexity and further underscore the potential of multi-catalytic systems.

show abstract

“…Importantly, the method tolerates starting materials and nucleophilic reagents bearing a range of common functional groups, including secondary alcohols and ketones. The one-pot strategy offers advantages over tedious and wasteful stepwise approaches, − especially for sequences occurring through the aldehyde intermediates that are often prone to side reactions. In a greater perspective, the study demonstrates that sequential catalysis complements current strategies for the functionalization of strong C–H bonds that require enforcing conditions with limited applicability in fine-chemical synthesis or those that are burdened with limited control of chemo-, regio-, or stereoselectivity.…”

mentioning

confidence: 99%

Enantioselective α-Arylation of Primary Alcohols under Sequential One-Pot Catalysis

et al. 2021

View full text Add to dashboard Cite

Secondary benzylic alcohols (SBAs) and diarylmethanols (DAMs) are common structural motifs of biologically active and medicinally relevant compounds. Here we report their enantioselective synthesis by -arylation of primary aliphatic and benzylic alcohols under sequential catalysis integrating a Ru-catalyzed hydrogen-transfer oxidation and a Ru-catalyzed nucleophilic addition. The method is applicable to various alcohols and aryl nucleophiles tolerating a range of functional groups, including secondary alcohols, ketones, alkenes, esters, NH-amides, tertiary amines, aryl halides, and heterocycles.Secondary benzylic alcohols (SBAs) and diarylmethanols (DA Ms) constitute valuable synthetic intermediates and prevalent structural motifs of numerous natural products and bioactive compounds. 1,2 Therefore, protocols for their stereoselective synthesis from various accessible starting materials have attracted much attention over the years. Common approaches include potent asymmetric (transfer) hydrogenation of ketones 1,3,4 or 1,2-addition of aryl nucleophiles to aldehydes, 5,6 particularly useful for fine-chemical synthesis when such starting materials are available and do not require additional synthetic steps.Because aliphatic alcohols represent a class of abundant starting materials, increasing attention has been devoted to developing methods for their valorization through selective C−H bond functionalization. [7][8][9] In the context of SBAs, an elegant strategy for the enantioselective alkylation of -C−H bonds of primary benzylic alcohols with unsaturated hydrocarbons (e.g., dienes, enynes) was devised by Krische and co-workers (Scheme 1a). 10,11 The methods of the arylation of -C−H bonds of aliphatic alcohols in the Minisci-type reactions were also established. [12][13][14][15][16][17] (Scheme 1b). Unfortunately, these methods lead to racemic products, leaving the enantioselective -C−H arylation of alcohols unexplored.We have recently reported an enantioselective synthesis of SBAs from unsaturated alcohols and aryl boronic acids under sequential catalysis (Scheme 1c). 18 The one-pot sequence of an Ir-catalyzed isomerization of the starting material and a Ru-catalyzed nucleophilic addition of an aryl boronic acid to the aldehyde intermediate provided a convenient synthetic method with a broad scope and functional group tolerance.

show abstract

One-pot strategy: A highly economical tool in organic synthesis and medicinal chemistry

Cited by 10 publications

References 183 publications

Multicatalytic Approach to One-Pot Stereoselective Synthesis of Secondary Benzylic Alcohols

Multicatalytic Approach to One-Pot Stereoselective Synthesis of Secondary Benzylic Alcohols

Challenges and Opportunities in Multicatalysis

Enantioselective α-Arylation of Primary Alcohols under Sequential One-Pot Catalysis

Contact Info

Product

Resources

About