Copper-Mediated Hydroxylation of Arenes and Heteroarenes Directed by a Removable Bidentate Auxiliary

Li, Xin; Liu, Yanhua; Gu, Wenjia; Li, Bo; Chen, Fa‐Jie; Shi, Bing‐Feng

doi:10.1021/ol5016064

Cited by 124 publications

(55 citation statements)

References 55 publications

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“…In 2014, Shi and co-workers designed a removable bidentate functional group, which could facilitate C–H hydroxylation of benzoic acids and heteroarenes [55]. An amidation reaction between benzoic acid and 2-(pyridine-2-yl)isopropylamine gave N -(2-(pyridine-2-yl)isopropyl)benzamides, which could be hydroxylated at the ortho position in moderate to excellent yields.…”

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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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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“…51 The method employed Ag 2 CO 3 as the oxidant and tetrabutylammonium iodide (TBAI) as the additive. Notably, the procedure could also proceed smoothly at a gram scale and was compatible with a wide range of functional groups.…”

Section: Carbon-oxygen Bond Formationmentioning

confidence: 99%

Recent advances in copper-mediated chelation-assisted functionalization of unactivated C–H bonds

2016

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Transition metal-catalyzed direct functionalization of C-H bonds has recently emerged as a powerful strategy for the construction of carbon-carbon and carbon-heteroatom bonds. Among various metals employed, base metal copper has attracted significant attention owing to its relatively low cost, abundance, and versatile reactivity. This review aims to comprehensively summarize the recent advances in copper-mediated (both stoichiometric and catalytic) chelation-assisted functionalization of unactivated C-H bonds.Scheme 1 Copper-mediated cross-coupling and C-H functionalization.

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“…70 The initial experiment was carried out with N -(2-(pyridin-2-yl-propan-2-yl)benzamide ( 180 ), Cu(OAc) 2 (1 equiv. ), Ag 2 CO 3 (2 equiv.…”

Section: C3–h-functionalizationmentioning

confidence: 99%

Recent advances in the C–H-functionalization of the distal positions in pyridines and quinolines

2015

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This review summarizes recent developments in the C–H-functionalization of the distal positions of pyridines, quinolines and related azaheterocycles. While the functionalization of the C2 position has been known for a long time and is facilitated by the proximity to N1, regioselective reactions in the distal positions are more difficult to achieve and have only emerged in the last decade. Recent advances in the transition metal-catalyzed distal C–H-functionalization of these synthetically-important azaheterocycles are discussed in detail, with the focus on the scope, site-selectivity and mechanistic aspects of the reactions.

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Copper-Mediated Hydroxylation of Arenes and Heteroarenes Directed by a Removable Bidentate Auxiliary

Cited by 124 publications

References 55 publications

Transition-metal-catalyzed synthesis of phenols and aryl thiols

Transition-metal-catalyzed synthesis of phenols and aryl thiols

Recent advances in copper-mediated chelation-assisted functionalization of unactivated C–H bonds

Recent advances in the C–H-functionalization of the distal positions in pyridines and quinolines

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