Rhodium‐Catalyzed <i>meta</i>‐C−H Functionalization of Arenes

Bera, Milan; Agasti, Soumitra; Chowdhury, Rajdip; Mondal, Rahul; Pal, Debasis

doi:10.1002/ange.201701579

Cited by 20 publications

(2 citation statements)

References 98 publications

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“…The mechanistic investigation suggests a meta‐ C−H bond activation through concerted metalation deprotonation (CMD) leading to the formation of a 12‐membered palladacycle as the key intermediate. Later in 2017, the Maiti group further demonstrated a Rh(I)‐catalyzed meta‐ C−H olefination of phenylacetic acid esters and benzylsulfonyl esters with complete mono‐selectivity utilizing 2‐hydroxy‐4‐methoxy benzonitrile template (T 8 ) [12b] . The protocol tolerates a wide range of electron‐deficient olefins and various functional groups attached to arenes.…”

Section: Nitrile‐directed C−h Bond Functionalizationsmentioning

confidence: 99%

The Renaissance of Organo Nitriles in Organic Synthesis

Rakshit

Dhara

Sahoo

et al. 2022

Chemistry An Asian Journal

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In the arena of functional group-oriented organic synthesis, nitrile or cyano functionality is of immense importance. The presence of nucleophilic N-atom, π-coordinating ability of the triple bond, and electrophilic C-center imparts unique and interesting reactivities. Owing to the ability of the nitrile to transform into various other functional groups or intermediates, the chemistry is very rich and diverse. In particular, the involvement of nitrile in numerous organic reactions such as inter-or intramolecular alkyne insertion, [2 + 2 + 2] cycloaddition with alkynes, [3 + 2] cycloaddition with azides, [4 + 2] cycloaddition with dienes allow the synthesis of many important carbo-and heterocycles. Furthermore, the nitrile serves as a directing group in many CÀ H bond functionalization reactions to introduce diverse functionalities and participate as a radical acceptor in radical cascade strategies to obtain a large variety of functional molecules. This review mainly focuses on the reactivity and diverse synthetic application of the nitrile including CÀ H bond functionalization, alkyne insertion, cycloaddition, and thermal or photochemical cascade strategy. The objective of the current review aims at bringing out the striking collection of various nitrile-triggered organic transformations.

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Section: Nitrile‐directed C−h Bond Functionalizationsmentioning

confidence: 99%

The Renaissance of Organo Nitriles in Organic Synthesis

Rakshit

Dhara

Sahoo

et al. 2022

Chemistry An Asian Journal

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“…[2,3] Recently, intensive efforts towards functionalization of remote meta-C(sp 2 )ÀHbonds have been reported. Direct functionalization of meta-C À Hbonds has been achieved exclusively by virtue of the differentiation of sterically or electronically biased properties of arene substrates, [4] theu se of transient mediators [5] and directing templates, [6] and other approaches. [7] Particularly,t he template-based methodology developed by the group of Yu provides an alternative strategy for metaselective C À Hf unctionalizations regardless of the substitution patterns and intrinsic electronic properties of the substrates.…”

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confidence: 99%

Activation of Remote meta‐C−H Bonds in Arenes with Tethered Alcohols: A Salicylonitrile Template

et al. 2017

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Palladium-catalyzed activation of remote meta-C-H bonds in arenes containing tethered alcohols was achieved with high regioselectivity by using a nitrile template. Computational studies on the macrocyclic transition state of the regioselectivity-determining C-H activation steps revealed that both the C-N-Ag angles and gauche comformations of phenyl ether play an extremely important role in the meta selectivity.

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Recent Developments in Remote Meta‐C−H Bond Functionalizations

Ali

Siddiqui

2021

Adv Synth Catal

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In the past decades, there has been a dramatic increase in the developments of novel methods for the activation/functionalization of inert C−H bonds as these protocols are not only competent, reduce the waste materials in addition to the reaction time and multiple steps but also allows the reaction to be carried out in a highly regio‐specific manner under operationally simple yet effective reaction conditions. Although, in recent years, a remarkable progress has been made in the field of ortho‐and para‐C−H bonds functionalization but to our best knowledge, the distal meta‐C−H activation/functionalization is still infancy and is yet to be explore to the advanced level. Hence, we feel that there is an urgent need to aware the research community about where the field of meta‐C−H functionalization stand at present and where it might be going in near future. To this context, we strive to compile the significant achievements made in the selective meta‐C−H bonds functionalization since 2018 to till date. More interestingly, we have also displayed an overview of the earlier reports related to the meta‐C−H activation/functionalization at the beginning of this particular manuscript, and hopefully the present review article will open diverse opportunities for the advancement of both academia as well as industry.

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Rhodium‐Catalyzed meta‐C−H Functionalization of Arenes

Cited by 20 publications

References 98 publications

The Renaissance of Organo Nitriles in Organic Synthesis

The Renaissance of Organo Nitriles in Organic Synthesis

Activation of Remote meta‐C−H Bonds in Arenes with Tethered Alcohols: A Salicylonitrile Template

Recent Developments in Remote Meta‐C−H Bond Functionalizations

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