Regioselective palladium-catalyzed direct cross-coupling of coumarins with simple arenes

Min, Minsik; Hong, Sungwoo

doi:10.1039/c2cc34551j

Cited by 88 publications

(33 citation statements)

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“…In addition, simple coumarins have recently been used successfully in transition‐metal‐catalyzed direct C–H bond activation reactions with different nucleophiles 5. For example, the palladium‐catalyzed direct C‐4 regioselective arylation of coumarins has been reported by Jafarpour, Li and Hong using arylboronic acids5a,5b and simple arenes,5c respectively. Lately, elegant examples of catalytic direct C‐3 functionalization of coumarins have also been developed 5d–5f.…”

Section: Introductionmentioning

confidence: 99%

Copper‐Catalyzed Regioselective Cross‐Dehydrogenative Coupling of Coumarins with Benzylic C_sp3–H Bonds

2014

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Section: Introductionmentioning

confidence: 99%

Copper‐Catalyzed Regioselective Cross‐Dehydrogenative Coupling of Coumarins with Benzylic C_sp3–H Bonds

2014

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“…Hong disclosed a method for the intermolecular regioselective (C‐4) CDC of 2‐coumarins with unactivated arenes, allowing the construction of 4‐arylcoumarins (neoflavones) (Scheme ) …”

Section: C–h Activation Of 2‐coumarinsmentioning

confidence: 99%

Transition Metal Mediated C–H Activation of 2‐Pyrones, 2‐Pyridones, 2‐Coumarins and 2‐Quinolones

Prendergast

McGlacken

2018

Eur J Org Chem

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C–H activation has emerged as a viable alternative to traditional C–C bond forming reactions such as the Suzuki–Miyaura, Stille, Negishi and others. However, C–H activation is rarely employed in total synthesis or fine chemical manufacture, particularly as an end‐game strategy. This may be due to the harsh conditions typically required. For C–H activation to become a truly useful and versatile methodology, conditions must emerge which are applicable to compounds with multiple functionalities. In this review, we hope to inspire the chemistry community to focus their efforts on milder conditions for C–H activation and cross‐dehydrogenative coupling. To this end, we have focused on describing C–H activation as it has been applied to several classes of biologically interesting, but chemically sensitive motifs: the 2‐pyrones, 2‐pyridones, 2‐coumarins and 2‐quinolones.

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“…Furthermore, PivOH proved to be a solvent of choice in the DHRs of chromones and coumarins 34,35 as well as in dehydrogenative arene-arene coupling 36 . Therefore, we replaced acetic acid with pivalic acid (PivOH), in which 1b is better soluble and which has a higher boiling point, enabling a reaction at a higher temperature at atmospheric pressure.…”

Section: Dehydrogenative Heck Reaction (Dhr)mentioning

confidence: 99%

Aerobic Palladium(II)-Catalyzed Dehydrogenative Heck Reaction in the Synthesis of Pyrenyl Fluorophores. A Photophysical Study of β-Pyrenyl Acrylates in Solution and in the Solid State

et al. 2015

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An aerobic dehydrogenative Heck reaction of pyrene (1a) and 2,7-di-tert-butylpyrene (1b) with ethyl acrylate is reported. The reaction is catalyzed by a Pd(OAc)2/4,5-diazafluoren-9-one (DAF) system and takes place in acetic or pivalic acid as solvents at 110-130 °C. The reaction of 1a afforded a 6:1 mixture of C-1- and C-4-alkenylated pyrenes (2a and 3a, respectively) in 71% yield. In the case of 1b, only a C-4-substituted product (3b) was formed in 46% yield. Compounds 2a and 3a,b exhibited fluorescence in solution and in the solid state. In chloroform and THF solution the fluorescence maxima were in the range of 440-465 nm, and quantum yields decreased in the order 2a > 3a> 3b. In the solid state, 3a,b showed blue-green fluorescence (ΦF = 0.26 and 0.14, respectively), whereas 2a emitted yellow-green fluorescence) (ΦF = 0.35). Besides blue-emitting monomers, the presence of green-emitting aggregated species (preformed dimers) in the crystals of 3a,b and red-emitting dynamic excimers in the crystals of 2a has been demonstrated. Single-crystal X-ray diffraction analyses of 2a and 3b confirmed π-stacking of pyrenyl moieties in the crystals of the former and the absence of stacking in the crystals of the latter compound.

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Regioselective palladium-catalyzed direct cross-coupling of coumarins with simple arenes

Abstract: An efficient method for the C4-regiocontrolled C-H functionalization of coumarins to enable facile oxidative cross-couplings with simple arene components is disclosed.

Cited by 88 publications

References 50 publications

Copper‐Catalyzed Regioselective Cross‐Dehydrogenative Coupling of Coumarins with Benzylic C_sp3–H Bonds

Copper‐Catalyzed Regioselective Cross‐Dehydrogenative Coupling of Coumarins with Benzylic C_sp3–H Bonds

Transition Metal Mediated C–H Activation of 2‐Pyrones, 2‐Pyridones, 2‐Coumarins and 2‐Quinolones

Aerobic Palladium(II)-Catalyzed Dehydrogenative Heck Reaction in the Synthesis of Pyrenyl Fluorophores. A Photophysical Study of β-Pyrenyl Acrylates in Solution and in the Solid State

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Regioselective palladium-catalyzed direct cross-coupling of coumarins with simple arenes

Abstract: An efficient method for the C4-regiocontrolled C-H functionalization of coumarins to enable facile oxidative cross-couplings with simple arene components is disclosed.

Cited by 88 publications

References 50 publications

Copper‐Catalyzed Regioselective Cross‐Dehydrogenative Coupling of Coumarins with Benzylic Csp3–H Bonds

Copper‐Catalyzed Regioselective Cross‐Dehydrogenative Coupling of Coumarins with Benzylic Csp3–H Bonds

Transition Metal Mediated C–H Activation of 2‐Pyrones, 2‐Pyridones, 2‐Coumarins and 2‐Quinolones

Aerobic Palladium(II)-Catalyzed Dehydrogenative Heck Reaction in the Synthesis of Pyrenyl Fluorophores. A Photophysical Study of β-Pyrenyl Acrylates in Solution and in the Solid State

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Copper‐Catalyzed Regioselective Cross‐Dehydrogenative Coupling of Coumarins with Benzylic C_sp3–H Bonds

Copper‐Catalyzed Regioselective Cross‐Dehydrogenative Coupling of Coumarins with Benzylic C_sp3–H Bonds