Copper-Mediated Dehydrogenative Biaryl Coupling of Naphthylamines and 1,3-Azoles

Odani, Riko; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro

doi:10.1021/jo402078q

Cited by 117 publications

(39 citation statements)

References 112 publications

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“…Along with the arylation, the group of Punniyamurthy reported a copper catalyzed C8‐introduction of indoles, pyrazoles and pyrroles, while the group of Miura developed a copper‐mediated C8‐azolation of naphthylamines (Scheme ) …”

Section: C8‐functionalization Of Naphthalene Derivativesmentioning

confidence: 99%

“…Along with the arylation, the group of Punniyamurthy reported a copper catalyzed C8-introduction of indoles, pyrazoles and pyrroles, [19] while the group of Miura developed a copper-mediated C8-azolation of naphthylamines (Scheme 8). [20] Naphthylamines are compatible with a lot of CÀ H activation reactions and, for instance, Ilies and Nakamura reported an iron-catalyzed methylation of naphthylamide 12 with trimethylaluminium as alkylating agent (Scheme 9). [21] C8-methylated naphthalene 15 was isolated in an excellent yield of 97 %.…”

Section: Bidentate Directing Groups: Picolinamide Derivativesmentioning

confidence: 99%

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Regioselective C−H Functionalization of Naphthalenes: Reactivity and Mechanistic Insights

Prévost

2020

ChemPlusChem

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Naphthalene is a very important skeleton in chemistry as evidenced by the large number of active compounds that contain it. For this reason, methods that can achieve easy functionalization of naphthalene derivatives are of great importance. This Minireview summarizes reactions that allow regioselective functionalization of 1‐substituted naphthalenes based on directed C−H activation strategies. Indeed, over the past ten years, many research groups have tried to develop new methodologies to directly introduce different functional groups on every position of naphthalene. In addition to the possible reactions reported in the literature, special attention has been paid to mechanistic aspects in order to explain the observed regioselectivities.

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Section: C8‐functionalization Of Naphthalene Derivativesmentioning

confidence: 99%

Section: Bidentate Directing Groups: Picolinamide Derivativesmentioning

confidence: 99%

Regioselective C−H Functionalization of Naphthalenes: Reactivity and Mechanistic Insights

Prévost

2020

ChemPlusChem

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“…[10] Optimization studies revealed that the use of acid as additive was essential for the reaction to take place.A mong the various carboxylic acids screened, PivOH provedt ob et he most effective one. Notably,t he direct arylation occurred site-selectively at the C-8 positiono f1 -naphthylamide but not at the position ortho to the amide group,p ossibly resulting from the preferable formation of af ive-membered metallacycle.…”

Section: Scheme2screeningo Fdirectinggroupsmentioning

confidence: 99%

Copper‐Catalyzed or ‐Mediated CH Bond Functionalizations Assisted by Bidentate Directing Groups

2016

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Copper salts, which are abundant, relatively inexpensive and possess low toxicity,h ave long been useda sv ersatile catalysts for various reactions in organic synthesis.R ecently,t he development of Cu-catalyzed or -mediated C À Hf unctionalization reactions has gaineds ignificant attention. Since the pioneering work of Daugulis on the introduction of 8-aminoquinoline and picolinic acid auxiliariesa sr emovable directing groups in transitionm etal-catalyzed C À Hb onda ctivations,t he combination of copper saltsw ith these bidentated irecting groups has emerged as an innovatives trategyf or the construction of carbon-carbon or carbon-heteroatom bonds through C À Hb ond cleavage.I na ddition to the 8-aminoquinoline and picolinamides ystems,s everal other bidentate directing groups including the 2-aminophenyloxazoline group by Yu andD ai andt he PIP systemb yS hi, have been developeda sw ell. This review intends to cover most of the recent advances on copper-catalyzed or -mediatedd irect sp 2 and sp 3 C À Hb ondf unctionalizations assisted by these bidentate directing groups.T he major achievements in this area are discussed and catalogued by the type of bonds formed (C À C, C À O, C À N, C À S, C À Pe tc.). Special attention is paid to the reaction mechanisms.S electede xamples of substrates are listed as well. In addition, apersonal outlook is given at the end.1I ntroduction 2C À CB ond Formation 3C À OB ond Formation 4C À NBond Formation 5C À SBond Formation 6C À PBondF ormation 7C À X(X= F, Cl, Br,I )BondF ormation 8I ntermolecularC À HA ctivation-Cyclization Tandem Reactions 9S ummary andOutlook

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“…The related dehydrogenative biaryl couplings of indoles, benzamides, and naphthylamines also proceed in the presence of Cu(OAc) 2 , with the assistance of appropriate directing groups, to make the corresponding bi(hetero)aryl linkages efficiently (Eqs. 15-17) [35][36][37]. The directors except for the 2-phenylpyridine are readily attachable and detachable: 2-pyrimidyl (Eq.…”

Section: Arylationmentioning

confidence: 99%

Copper-Mediated Intermolecular C–H/C–H and C–H/N–H Couplings via Aromatic C–H Cleavage

Hirano

Miura

2015

Topics in Organometallic Chemistry

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Copper salts and complexes have recently received significant attention as less expensive and abundant alternatives to some noble transition metal catalysts such as palladium, rhodium, and ruthenium, in the research field of C-H activation. They not only replace the above precious metal catalysts in the known C-H transformations but also mediate unique, otherwise challenging, cross-coupling reactions involving C-H bond cleavage. This chapter mainly focuses on recent advances in the copper-mediated or copper-catalyzed intermolecular C-H/C-H and C-H/N-H aromatic couplings. Seminal mechanistic studies on the copper-mediated C-H functionalization are also discussed.

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Copper-Mediated Dehydrogenative Biaryl Coupling of Naphthylamines and 1,3-Azoles

Cited by 117 publications

References 112 publications

Regioselective C−H Functionalization of Naphthalenes: Reactivity and Mechanistic Insights

Regioselective C−H Functionalization of Naphthalenes: Reactivity and Mechanistic Insights

Copper‐Catalyzed or ‐Mediated CH Bond Functionalizations Assisted by Bidentate Directing Groups

Copper-Mediated Intermolecular C–H/C–H and C–H/N–H Couplings via Aromatic C–H Cleavage

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