One‐Pot Synthesis of 3‐Alkylidenephthalides from Benzoic Acids by a Rhodium‐Catalyzed <i>ortho</i>‐CH Acylation Process

Danoun, Grégory; Mamone, Patrizia; Gooßen, Lukas J.

doi:10.1002/chem.201303426

Cited by 35 publications

(15 citation statements)

References 63 publications

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“…More importantly, the carboxyl group is able to capture the intermediates to afford oxygen heterocycle motifs . In this context, as shown in Scheme , Gooßen synthesized 3‐alkylidenephthalides (a mixture of Z ‐ and E ‐isomers) from benzoic acids or aliphatic acids and anhydrides via a one‐pot C−H acylation/elimination cascade reaction . Lee et al.…”

Section: Methodsmentioning

confidence: 99%

“…[10] More importantly, the carboxyl group is able to capture the intermediates to afford oxygen heterocycle motifs. [12] Lee et al reported the palladium-catalyzed tandem CÀH olefination and oxidative coupling of ortho-substituted benzoic acids with vinylarenes to produce (Z)-3-benzylidenephthalides. [12] Lee et al reported the palladium-catalyzed tandem CÀH olefination and oxidative coupling of ortho-substituted benzoic acids with vinylarenes to produce (Z)-3-benzylidenephthalides.…”

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confidence: 99%

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Rhodium(III)‐Catalyzed Tandem C−H Olefination and Oxidative Cyclization of Aromatic Acids with Acrylates for the Synthesis of (E)‐3‐Ylidenephthalides

Han

Fan

et al. 2017

Adv Synth Catal

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Intermolecular tandem CÀH olefination/ CÀO cyclization has been achieved via a rhodium (III)-catalyzed CÀH activation of carboxylic acids with acrylates. This strategy provides the direct and efficient construction of biologically relevant (E)-3ylidenephthalide scaffolds with satisfactory to good yields, and is characterized by stoichiometric reactants, exclusive stereoselectivity, commercially available substrates, mild atmospheric conditions, and short reaction time (less than 2 h).

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Rhodium(III)‐Catalyzed Tandem C−H Olefination and Oxidative Cyclization of Aromatic Acids with Acrylates for the Synthesis of (E)‐3‐Ylidenephthalides

Han

Fan

et al. 2017

Adv Synth Catal

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“…The same year, Gooßen and co‐workers synthesized 3‐alkylidenephthalides by a carboxylate‐directed olefination via a one‐pot C−H acylation/acylalization/elimination cascade (Scheme ) . Importantly, they showed that the transformation can be achieved from two carboxylic acids by using pivalic anhydride as an activating agent.…”

Section: C−c Bond Formationmentioning

confidence: 99%

Carboxylic Acids as Directing Groups for C−H Bond Functionalization

Drapeau

Gooßen

2016

Chemistry A European J

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269

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The selective transformation of C-H bonds is one of the most desirable approaches to creating complexity from simple building blocks. Several directing groups are efficient in controlling the regioselectivity of catalytic C-H bond functionalizations. Among them, carboxylic acids are particularly advantageous, since they are widely available in great structural diversity and at low cost. The carboxylate directing groups can be tracelessly cleaved or may serve as the anchor point for further functionalization through decarboxylative couplings. This Minireview summarizes the substantial progress made in the last few years in the development of reactions in which carboxylate groups direct C-H bond functionalizations with formation of C-C, C-O, C-N, or C-halogen bonds at specific positions. It is divided into sections on C-C, C-O, C-N, and C-halogen bond formation, each of which is subdivided by reactions and product classes. Particular emphasis is placed on methods that enable multiple derivatizations by combining carboxylate-directed C-H functionalization with decarboxylative couplings.

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“…[1] During the preparation of the review, the Gooßen group reported the ortho-acylation of benzoic acids to form o-acyl benzoic acids, Scheme C1, [2] and 3-alkylidenephthalides, Scheme C2. [3] The authors apologize that this work was overlooked.…”

Section: Cover Picturesmentioning

confidence: 99%

Graphical Abstract: Adv. Synth. Catal. 8/2014

2014

Adv Synth Catal

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One‐Pot Synthesis of 3‐Alkylidenephthalides from Benzoic Acids by a Rhodium‐Catalyzed ortho‐CH Acylation Process

Abstract: Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/chem.201303426. Figure 1. Examples of biologically active alkylidenephthalides. Scheme 1. Synthetic entries to alkylidenephthalides.

Cited by 35 publications

References 63 publications

Rhodium(III)‐Catalyzed Tandem C−H Olefination and Oxidative Cyclization of Aromatic Acids with Acrylates for the Synthesis of (E)‐3‐Ylidenephthalides

Rhodium(III)‐Catalyzed Tandem C−H Olefination and Oxidative Cyclization of Aromatic Acids with Acrylates for the Synthesis of (E)‐3‐Ylidenephthalides

Carboxylic Acids as Directing Groups for C−H Bond Functionalization

Graphical Abstract: Adv. Synth. Catal. 8/2014

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