Ruthenium(II)-Catalyzed Synthesis of Hydroxylated Arenes with Ester as an Effective Directing Group

Yang, Yiqing; Lin, Yun; Rao, Yu

doi:10.1021/ol301104n

Cited by 140 publications

(50 citation statements)

References 86 publications

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“…[39] Examples of oxidation and olefination were reported with ester and ketone as directing group but in both cases a mixture of C2-and C8-functionalized products were obtained (Scheme 21.b,c). [40,41] Despite one example of halogenations reported in 2013, [42] carbonyl-directed C8-functionalization is quite rare in the literature. In 2016, Xia and Fu's team developed a palladiumcatalyzed C8-triflation of naphthalenes (Scheme 22).…”

Section: -Carbonylnaphthalene Derivatives In C8-functionalizationmentioning

confidence: 99%

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: -Carbonylnaphthalene Derivatives In C8-functionalizationmentioning

confidence: 99%

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

Prévost

2020

ChemPlusChem

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“…They reported the first ortho -hydroxylation of ethyl benzoates in 2012 [79]. Both electron-rich and electron-deficient ethyl benzoates were readily converted to the corresponding hydroxylated products.…”

Section: Reviewmentioning

confidence: 99%

Transition-metal-catalyzed synthesis of phenols and aryl thiols

Liu¹,

Li²,

Yan³

2017

Beilstein J. Org. Chem.

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Phenols and aryl thiols are fundamental building blocks in organic synthesis and final products with interesting biological activities. Over the past decades, substantial progress has been made in transition-metal-catalyzed coupling reactions, which resulted in the emergence of new methods for the synthesis of phenols and aryl thiols. Aryl halides have been extensively studied as substrates for the synthesis of phenols and aryl thiols. In very recent years, C–H activation represents a powerful strategy for the construction of functionalized phenols directly from various arenes. However, the synthesis of aryl thiols through C–H activation has not been reported. In this review, a brief overview is given of the recent advances in synthetic strategies for both phenols and aryl thiols.

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“…These methods mainly include three kinds of strategies: (a) rearrangement of aromatic O–X bonds151617181920; (b) directing group-assisted ortho C–H hydroxylation of arenes21222324252627; and (c) ortho C–H functionalization of phenols2829303132. Although these results have promoted the development of the phenol chemistry, the more efficient, economical and biocompatible methods are still in demand.…”

mentioning

confidence: 99%

A bioinspired and biocompatible ortho-sulfiliminyl phenol synthesis

et al. 2017

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Synthetic methods inspired by Nature often offer unique advantages including mild conditions and biocompatibility with aqueous media. Inspired by an ergothioneine biosynthesis protein EgtB, a mononuclear non-haem iron enzyme capable of catalysing the C–S bond formation and sulfoxidation, herein, we discovered a mild and metal-free C–H sulfenylation/intramolecular rearrangement cascade reaction employing an internally oxidizing O–N bond as a directing group. Our strategy accommodates a variety of oxyamines with good site selectivity and intrinsic oxidative properties. Combining an O–N bond with an X–S bond generates a C–S bond and an S=N bond rapidly. The newly discovered cascade reaction showed excellent chemoselectivity and a wide substrate scope for both oxyamines and sulfenylation reagents. We demonstrated the biocompatibility of the C–S bond coupling reaction by applying a coumarin-based fluorogenic probe in bacterial lysates. Finally, the C–S bond coupling reaction enabled the first fluorogenic formation of phospholipids, which self-assembled to fluorescent vesicles in situ.

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Ruthenium(II)-Catalyzed Synthesis of Hydroxylated Arenes with Ester as an Effective Directing Group

Cited by 140 publications

References 86 publications

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

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

Transition-metal-catalyzed synthesis of phenols and aryl thiols

A bioinspired and biocompatible ortho-sulfiliminyl phenol synthesis

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