Palladium-catalyzed mono-γ-arylation of 7-methoxy-4-methylcoumarin

Sexton, Mary; Okazaki, Ami; Yu, Zhuowen; Venrooy, Alexis van; Schmink, Jason R.; Malachowski, William P.

doi:10.1016/j.tetlet.2019.151057

Cited by 6 publications

(3 citation statements)

References 29 publications

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“…In 1998, Miura and co‐workers described a palladium‐catalyzed γ‐arylation of α,β‐unsaturated aldehydes with aryl bromides [5] . Since then, a number of α,β‐unsaturated aldehydes, [6] ketones, [3b,7] amides [8] and esters [9] were applied in such transformations (Scheme 1a). In the meantime, a few cascade reactions were also developed.…”

Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Tandem γ‐Arylation/Aromatization of Cyclohex‐2‐En‐1‐One Derivatives: A Route to 3,4‐Dihydroanthracen‐1(2H)‐Ones

Song

Zhang

et al. 2021

Adv Synth Catal

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Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Tandem γ‐Arylation/Aromatization of Cyclohex‐2‐En‐1‐One Derivatives: A Route to 3,4‐Dihydroanthracen‐1(2H)‐Ones

Song

Zhang

et al. 2021

Adv Synth Catal

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“…In 2019, Malachowski and co-workers reported the palladium-catalyzed selective mono-γ-arylation of 7-methoxyl-4-methylcoumarin (Scheme 7 ). 17 The Buchwald G3 precatalyst, in conjunction with either the Xantphos or N -Xantphos, was found to be highly effective in this reaction with aryl iodides, bromides, chlorides, and triflates. A wide range of functional groups was well tolerated, and heterocyclic substrates were also found to be feasible cross-coupling partners.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Site-Selective Arylation of α,β-Unsaturated Carbonyl Compounds through a Ligand-Controlled Strategy

Yuen

2022

Synlett

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Palladium-catalyzed direct arylation of α,β-unsaturated carbonyl compounds is an efficient and attractive strategy to access arylated α,β-unsaturated carbonyl compounds through the construction of carbon–carbon bonds. This reaction has several challenges, especially in terms of the control of regioselectivity between α- and γ-arylation and the selectivity for monoarylation and multiple arylation. Herein, we discuss the recent development of γ-arylation of α,β-unsaturated carbonyl compounds and present the ligand-controlled, site-selective α- and γ-arylation of α,β-unsaturated carbonyl ketones with (hetero)aryl halides. The site selectivity of the reaction is switchable by simply changing the phosphine ligand.1 Introduction2 Reaction Development and Mechanistic Investigation3 Conclusion and Outlook

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“…Lignans and related compounds, which are biosynthesized by the coupling of two phenylpropanoid (C6-C3) units, have been isolated from many kinds of plants containing dietary plants. − The isolation and pharmaceutical, synthetic, and chemical research of coumarino-lignans − and phenylalkylcoumarin-lignan-related compounds − have been reported. We decided to promote the agrochemical and phytochemical study of these compounds.…”

mentioning

confidence: 99%

Plant Growth Suppressive Activity of (R)-3-(7′-Aryl-9′-hydroxyprop-8′-yl)coumarin, Structural Isomer of Z-2-Hydroxybenzylidene-γ-butyrolactone-type Lignan

Sartiva

Ishida

Yoneyama

et al. 2022

J. Agric. Food Chem.

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3-(7′-Aryl-9′-hydroxyprop-8′-yl)coumarin, which is a structural isomer of a Z-2-hydroxybenzylidene-γ-butyrolactone-type lignan, was stereoselectively synthesized and subjected to plant growth regulation examination. (R)-4′-Methoxyphenyl derivative 3 showed stereospecific plant growth suppressive activity. The significance of the presence of hydroxy group at the 9′-position for the activity was clarified. The effect of the substituent at the 7′-aryl group was also shown. The 3′-methoxy, 4′-methoxy, and 4′-trifluoromethyl derivatives 10, 3, and 22 led to the most significant growth suppression of Italian ryegrass roots. The 2′-methoxy derivative 9 and 4′-methoxy derivative 3 provided the most growth suppressive activity against lettuce shoots and roots, respectively.

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Palladium-catalyzed mono-γ-arylation of 7-methoxy-4-methylcoumarin

Cited by 6 publications

References 29 publications

Palladium‐Catalyzed Tandem γ‐Arylation/Aromatization of Cyclohex‐2‐En‐1‐One Derivatives: A Route to 3,4‐Dihydroanthracen‐1(2H)‐Ones

Palladium‐Catalyzed Tandem γ‐Arylation/Aromatization of Cyclohex‐2‐En‐1‐One Derivatives: A Route to 3,4‐Dihydroanthracen‐1(2H)‐Ones

Palladium-Catalyzed Site-Selective Arylation of α,β-Unsaturated Carbonyl Compounds through a Ligand-Controlled Strategy

Plant Growth Suppressive Activity of (R)-3-(7′-Aryl-9′-hydroxyprop-8′-yl)coumarin, Structural Isomer of Z-2-Hydroxybenzylidene-γ-butyrolactone-type Lignan

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