Ruthenium-Catalyzed Para-Selective Oxidative Cross-Coupling of Arenes and Cycloalkanes

Guo, Xiangyu; Li, Chao‐Jun

doi:10.1021/ol202081c

Cited by 126 publications

(43 citation statements)

References 30 publications

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“…[195] Thec ombination of Ru 3 (CO) 12 and 1,2-bis(diphenylphosphino)benzene (DPPBenzene) as acatalytic system with di-tertbutylperoxide (DTPB) as the oxidant promotes the radical addition of cyclic alkanes with moderate to good efficiency. [195] Thec ombination of Ru 3 (CO) 12 and 1,2-bis(diphenylphosphino)benzene (DPPBenzene) as acatalytic system with di-tertbutylperoxide (DTPB) as the oxidant promotes the radical addition of cyclic alkanes with moderate to good efficiency.…”

Section: Alkylation By Cross-dehydrogenative Coupling With Alkanes Ementioning

confidence: 99%

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

2019

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The alkylation of arenes is one of the most fundamental transformations in chemical synthesis leading to privileged scaffolds in many areas of science. Classical methods for the introduction of alkyl groups to arenes are mostly based on the Friedel-Crafts reaction, radical additions, metallation or pre-functionalization of the arene: these methods however suffer from limitations in scope, efficiency and selectivity. Moreover, they are based on the innate reactivity of the starting arene, favoring the alkylation at a certain position and rendering the introduction of alkyl chains at other positions much more challenging. This can be addressed by the use of a directing group facilitating, in the presence of a metal catalyst, the regioselective alkylation of a C-H bond. These directed alkylations of C-H bonds in arenes are overviewed, in a comprehensive manner, in this review article.

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Section: Alkylation By Cross-dehydrogenative Coupling With Alkanes Ementioning

confidence: 99%

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

2019

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“…21 Using [Ru 3 (CO) 12 ] and 1,4-bis(diphenylphosphino)butane (dppb) in the presence of di-tert-butyl peroxide (TBP), various arenes were functionalized with simple cycloalkanes (Scheme 16). 21 In 2004, Sames' group reported an iridium-catalyzed intramolecular cyclization of a pyrrolidine-containing alkene-amide under neutral and catalytic conditions (Scheme 17). 22 The key advance made with this reaction was the ability to promote carbon-hydrogen bond activation and alkene insertion in tandem and in preference to α-hydride elimination.…”

Section: Scheme 14 Copper-catalyzed Cross-dehydrogenative Arylationmentioning

confidence: 99%

Advances in Transition-Metal-Catalyzed Direct sp3-Carbon–Hydrogen Bond Functionalization

Zhang

Wang

Xing

2015

Synlett

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Transition-metal-catalyzed direct carbon-hydrogen bond functionalization has made significant advances in the field of carbonhydrogen bond activation over the past decades. This methodology has the potential to be used in many different areas of chemistry; for example, it can provide an opportunity for the synthesis of various kinds of complex compounds. This account mainly focuses on recent advances in transition-metal-catalyzed direct sp 3 -carbon-hydrogen bond functionalization to form carbon-carbon bonds. 1 Introduction 2 Carbon-Carbon Bond Formation via Direct sp 3 -Carbon-Hydrogen Bond Functionalization 2.1 Coupling of sp 3 -Carbon-Hydrogen and sp-Carbon-Hydrogen Bonds 2.2 Coupling of sp 3 -Carbon-Hydrogen and sp 2 -Carbon-Hydrogen Bonds 2.3 Coupling of sp 3 -Carbon-Hydrogen and sp 3 -Carbon-Hydrogen Bonds 2.4 Coupling of sp 3 -Carbon-Hydrogen and C-X Bonds 3 Conclusion Key words transition metals, catalysis, carbon-carbon bond formations, cross-dehydrogenative coupling, direct bond functionalizations Carbon-Carbon Bond Formation via Direct sp 3 -Carbon-Hydrogen Bond FunctionalizationThe oxidative coupling of two different carbon-hydrogen bonds was termed cross-dehydrogenative coupling (CDC) by Li's group 4 in 2004, and it has become an increasing field of interest. In the past decade, a growing number of efficient procedures and novel methods have been introduced. These methods make the connection of sp 3 -carbonhydrogen with sp-carbon-hydrogen, sp 2 -carbon-hydrogen, sp 3 -carbon-hydrogen, and C-X bonds a reality (Scheme 1). 4,5 However, the development of chemo-, regio-, and stereoselective sp 3 -carbon-carbon bond formation reactions is still one of the most challenging tasks in organic synthesis.

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“…With Ruthenium In 2011, Guo and Li [106] reported the para-selective CDC reaction of arenes with cycloalkanes (Scheme 4.18). In this case, a radical mechanism was involved, and as we saw previously, there were issues with the positional selectivity in some cases.…”

Section: Non-dmg Assisted Ar/alkyl Couplings C(sp 2 )-H Activationsmentioning

confidence: 99%

“…The Ru-catalyzed CDC direct alkylation of arenes with cycloalkanes by Guo and Li [106]. Many further examples of Cu-catalysis in this process are described [108].…”

Section: Scheme 418mentioning

confidence: 99%

C–H Bond Activation for Arylations

2014

Catalytic Arylation Methods

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Ruthenium-Catalyzed Para-Selective Oxidative Cross-Coupling of Arenes and Cycloalkanes

Cited by 126 publications

References 30 publications

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

Advances in Transition-Metal-Catalyzed Direct sp3-Carbon–Hydrogen Bond Functionalization

C–H Bond Activation for Arylations

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