Catechol

Barner, Bruce A.; Bongat, Aileen F. G.; Demchenko, Alexei V.

doi:10.1002/047084289x.rc031.pub2

Cited by 3 publications

(3 citation statements)

References 31 publications

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“…Catechols are important functional groups of many naturally occurring small molecules and materials (Figure A). , They are also building blocks for agrochemicals, pharmaceuticals, perfumes, and resins, making their functionalization an important step in the chemical value chain. − Electrophilic aromatic substitution (E Ar S) and nucleophilic displacement reactions are among the most common ways to functionalize the C–H and O–H bonds, respectively (Figure B, left). ,, Both employ catechols as nucleophiles, and are thus limited to electrophilic coupling partners, and both can suffer poor regioselectivity . They also frequently employ stoichiometric amounts of activators or require an equivalent of base, creating an undesirable waste stream.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Aerobic Cross-Dehydrogenative Coupling of Phenols and Catechols

Huang

et al. 2019

ACS Catal.

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We describe a selective, catalytic aerobic cross-dehydrogenative coupling (CDC) reaction of phenols and catechols that creates aryl ethers. To avoid challenges of selectivity, we employ copper (Cu) coordination to confine substrate redox to the inner coordination sphere of the metal. This minimizes nonselective radical processes to provide high levels of selectivity for cross over homo coupling, by C–O instead of C–C bond formation. The method remains efficient on synthetically useful substrates and scales and enables a convergent synthesis of the tetrahydroisoquinoline alkaloid (S, S)-thalicarpine featuring diaryl ether formation in the late stages of the synthesis. Related molecules are difficult to prepare by traditional Ullman-type coupling and provide a benchmark for evaluating the potential utility of our methodology.

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Section: Introductionmentioning

confidence: 99%

Catalytic Aerobic Cross-Dehydrogenative Coupling of Phenols and Catechols

Huang

et al. 2019

ACS Catal.

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“…Catechols are redox-active, electron rich aromatic rings that are commonly found in natural products, pharmaceuticals and naturally occurring materials . They are also important intermediates in organic synthesis that are most frequently used as nucleophiles in redox neutral substitution reactions.…”

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confidence: 99%

Total Synthesis of (S)-Cularine via Nucleophilic Substitution on a Catechol

Huang

Lumb

2020

Org. Lett.

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Catechols are part of many essential chemicals and are valuable, typically nucleophilic intermediates used in synthesis. Here we describe an unexpected transformation in which they play the role of the electrophile in a formal nucleophilic aromatic substitution. We made this discovery while studying a seven-membered dioxepin ring formation during a synthesis of the benzyltetrahydroisoquinoline (S)-cularine. We suggest a chain mechanism for this new transformation that is triggered by molecular oxygen and that propagates an electrophilic ortho-quinone.

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“…(Figure ). Recently, pyrocatechols have aroused widespread interest by medicinal and synthetic chemists due to their use as a class of efficient synthons for the synthesis and late-stage functionalization of potential drug candidates . However, the preparation of pyrocatechols by transition-metal catalysis is limited in the exploration of palladium .…”

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confidence: 99%

Cobalt-Catalyzed C–H Acetoxylation of Phenols with Removable Monodentate Directing Groups: Access to Pyrocatechol Derivatives

et al. 2020

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An efficient cobalt-catalyzed C–H acetoxylation of phenols has been developed by using PIDA (phenyliodine diacetate) as a sole acetoxy source to synthesize pyrocatechol derivatives for the first time. The key feature of this method is the use of earth-abundant metal cobalt as the green and inexpensive catalyst for the acetoxylation of C(sp2)–H bonds under neutral reaction conditions. Furthermore, the gram-scale reaction and late-stage functionalization demonstrated the usefulness of this method.

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Catechol

Cited by 3 publications

References 31 publications

Catalytic Aerobic Cross-Dehydrogenative Coupling of Phenols and Catechols

Catalytic Aerobic Cross-Dehydrogenative Coupling of Phenols and Catechols

Total Synthesis of (S)-Cularine via Nucleophilic Substitution on a Catechol

Cobalt-Catalyzed C–H Acetoxylation of Phenols with Removable Monodentate Directing Groups: Access to Pyrocatechol Derivatives

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