Regioselective Palladium-Catalyzed C-H Bond Trifluoroethylation of Indoles: Exploration and Mechanistic Insight

Zhang, Hao; Wang, Haoyang; Luo, Yixin; Chen, Chaohuang; Cao, Yimiao; Chen, Pinhong; Guo, Yinlong; Lan, Yu; Liu, Guosheng

doi:10.1021/acscatal.7b03220

Cited by 91 publications

(43 citation statements)

References 67 publications

(16 reference statements)

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“…Recently, Liu and co‐workers utilized this strategy for the selective C2 trifluoroethylation of indoles with commercially available trifluoroethyl iodide as the alkylating reagent (Scheme a). The reaction displays a wide functional group tolerance, and can even be utilized for the late‐stage trifluoroethylation of complex indole derivatives (Scheme b).…”

Section: C2 Functionalization Of Nh‐indoles and Nh‐pyrrolesmentioning

confidence: 99%

Palladium(II)‐Initiated Catellani‐Type Reactions

et al. 2019

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The Catellani reaction is known as a powerful strategy for the expeditious synthesis of highly substituted arenes and benzo‐fused rings, which are usually difficult to access through traditional cross‐coupling strategies. It utilizes the synergistic interplay of palladium and norbornene catalysis to facilitate sequential ortho C−H functionalization and ipso termination of aryl halides in a single operation. In classical Catellani‐type reactions, aryl halides are mainly used as the substrates, and a Pd0 catalyst is required to initiate the reaction. Nevertheless, recent advances showcase that Catellani‐type reactions can also be initiated by a PdII catalyst with different starting materials instead of aryl halides via different reaction mechanisms and under different conditions. This emerging concept of PdII/norbornene cooperative catalysis has significantly advanced Catellani‐type reactions, thus enabling future developments of this field. In this Minireview, PdII‐initiated Catellani‐type reactions and their application in the synthesis of bioactive molecules are summarized.

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Section: C2 Functionalization Of Nh‐indoles and Nh‐pyrrolesmentioning

confidence: 99%

Palladium(II)‐Initiated Catellani‐Type Reactions

et al. 2019

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“…Based on the analysis of the aforementioned results and previous reports, a plausible mechanism was proposed in Scheme 6 (Langlois et al, 1991; Ji et al, 2011; Zhang et al, 2018; Khan et al, 2019). Initially, the t -butoxy radical, generated from copper metal, reacts with CF 3 SO2- to provide •CF 3 SO 2 .…”

Section: Mechanismmentioning

confidence: 86%

Ligand- and Additive-Free 2-Position-Selective Trifluoromethylation of Heteroarenes Under Ambient Conditions

Shi

et al. 2019

Front. Chem.

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A highly selective copper-catalyzed trifluoromethylation of indoles is reported with the assistance of a removable directing group. This protocol provides an easy and rapid method to various 2-position-selective trifluoromethylated heteroarenes including indoles, pyrroles, benzofuran, and acetanilide. What is more, the reaction takes place at ambient conditions without any external ligand or additive.

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“…Furthermore, the Liu group reported an intriguing study on the direct C2−H trifluoroethylation of NH ‐indoles using palladium/norbornene system (Scheme 25). [47] This system is based on the Bach indole alkylation method [48] starting with aminopalladation of norbornene, and includes a β‐diketone ligand to accelerate the oxidative addition step. Through KIE ( k H / k D =1.1) and DFT studies, the authors proposed that the oxidative addition is likely the rate determining step.…”

Section: Transition‐metal‐catalyzed Functionalization At the C2 Positionmentioning

confidence: 99%

Recent Advances in Metal‐Catalyzed Functionalization of Indoles

et al. 2021

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Indole is one of the most important heterocycles in organic synthesis, natural products, and drug discovery. Recently, tremendous advances in the selective functionalization of indoles have been reported. Although the most important advances have been powered by transition metal catalysis, exceedingly useful methods in the absence of transition metals have also been reported. In this review, we provide an overview of functionalization reactions of indoles that have been published in the last years with a focus on the most recent advances, aims, and future trends. The review is organized by the positional selectivity and type of methods used for functionalization. In particular, we discuss major advances in transition‐metal‐catalyzed C−H functionalization at the classical C2/C3 positions, transition‐metal‐catalyzed C−H functionalization at the remote C4/C7 positions, transition‐metal‐catalyzed cross‐coupling, and transition‐metal‐free functionalization.

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Regioselective Palladium-Catalyzed C-H Bond Trifluoroethylation of Indoles: Exploration and Mechanistic Insight

Cited by 91 publications

References 67 publications

Palladium(II)‐Initiated Catellani‐Type Reactions

Palladium(II)‐Initiated Catellani‐Type Reactions

Ligand- and Additive-Free 2-Position-Selective Trifluoromethylation of Heteroarenes Under Ambient Conditions

Recent Advances in Metal‐Catalyzed Functionalization of Indoles

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