Synthesis of Triarylmethanes by Palladium-Catalyzed C–H/C–O Coupling of Oxazoles and Diarylmethanol Derivatives

Tabuchi, Sho; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro

doi:10.1021/jo5010636

Cited by 64 publications

(35 citation statements)

References 81 publications

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“…In addition to the above-discussed transformations,which are all based on traditional alkylating agents,s everal additional reactions based on other types of reagents have been reported for the direct alkylation of azole derivatives.T hey include carboxylic acids, [78][79][80][81]130] peroxides, [127,131] aldehydes, [86,87] in situ generated iminium ions, [132] N-tosylhydrazones, [133][134][135] benzyl carbonates, [136] diarylmethyl carbonates and pivalates, [137] carboxylic xanthates, [97,98] and tertiary cycloalkanols. [99] Carboxylic acids have indeed been exploited for the alkylation of azoles and were shown to be both attractive and efficient alkylating agents.W hereas the use of photoredox catalysis only allowed the direct alkylation of some specific azoles, [78][79][80][81] Zhaoss ilver-promoted oxidative alkylation of azoles such as (benzo)thiazoles and benzoxazole with alkylcarboxylic acids was shown to be more general, affording the corresponding secondary and tertiary C2-alkylated products in good to excellent yields (Scheme 42).…”

Section: Alkylation With Other Reagentsmentioning

confidence: 99%

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

2019

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The alkylation of arenes is one of the most fundamental transformations in chemical synthesis leading to privileged scaffolds in many areas of science. Classical methods for the introduction of alkyl groups to arenes are mostly based on the Friedel-Crafts reaction, radical additions, metallation or pre-functionalization of the arene: these methods however suffer from limitations in scope, efficiency and selectivity. Moreover, they are based on the innate reactivity of the starting arene, favoring the alkylation at a certain position and rendering the introduction of alkyl chains at other positions much more challenging. This can be addressed by the use of a directing group facilitating, in the presence of a metal catalyst, the regioselective alkylation of a C-H bond. These directed alkylations of C-H bonds in arenes are overviewed, in a comprehensive manner, in this review article.

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Section: Alkylation With Other Reagentsmentioning

confidence: 99%

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

2019

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“…Some other more specific processes have also been reported for the direct alkylation of azoles: these include the palladium‐catalyzed benzylation of azoles with benzyl carbonates, the palladium‐catalyzed cross‐coupling between (benz)oxazoles and diarylmethyl carbonates and pivalates, the metal‐free oxidative radical methylation and related alkylations of azoles with carboxylic xanthates, and the silver‐catalyzed C2‐alkylation of benzothiazoles and benzoxazoles with tertiary cycloalkanols …”

Section: Alkylation Of Heteroarenesmentioning

confidence: 99%

Beyond Friedel and Crafts: Innate Alkylation of C−H Bonds in Arenes

Evano

Theunissen

2019

Angew Chem Int Ed

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Alkylated arenes are ubiquitous molecules and building blocks commonly utilized in most areas of science where there is a need for small organic molecules. Despite its apparent simplicity, the regioselective alkylation of arenes is still a challenging transformation in a lot of cases. Classical methods for the introduction of alkyl groups on arenes, which include the venerable Friedel-Crafts reaction, radical additions, metallation or pre-functionalization of the arene, as well as alternatives such as the directed alkylation of C-H bonds, still suffer from severe limitations in terms of scope, efficiency and selectivity. This can be addressed by exploiting the innate reactivity of some (hetero)arenes, in which electronic and steric properties, governed (or not) by the presence of one (or multiple) heteroatom(s) ensure high levels of regioselectivity. These innate alkylations of C-H bonds in (hetero)arenes will be overviewed, in a comprehensive manner, in this review article.

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“…25 The reaction with benzoxazole or 5-substituted oxazoles gave a variety of unsymmetric triarylmethanes in good to excellent yields.…”

Section: Acs Catalysismentioning

confidence: 99%

Recent Advances in the Synthesis of Triarylmethanes by Transition Metal Catalysis

2015

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Triarylmethanes and related compounds are fascinating molecules because of their structural and physical properties, many potential applications in organic functional materials, and high biological activity. Recently, catalysis has provided new synthesis routes to triarylmethanes with high selectivity and diversity, including the possibility of preparing enantiomerically enriched derivatives, which is typically challenging using classical methods. This Perspective reviews recent advances in new synthesis approaches to triarylmethanes using well-defined transition metal catalysts. These methods will allow the development of new, unexplored triarylmethane structures.

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Synthesis of Triarylmethanes by Palladium-Catalyzed C–H/C–O Coupling of Oxazoles and Diarylmethanol Derivatives

Cited by 64 publications

References 81 publications

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

Beyond Friedel and Crafts: Innate Alkylation of C−H Bonds in Arenes

Recent Advances in the Synthesis of Triarylmethanes by Transition Metal Catalysis

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