Palladium(<scp>ii</scp>)-catalysed ortho-arylation of N-benzylpiperidines

Tan, Peng Hui; Haughey, Maxwell B.; Dixon, Darren J.

doi:10.1039/c5cc00410a

Cited by 27 publications

(15 citation statements)

References 43 publications

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“…2013 年, Zhang 课题组 [26] 同样以 N,N-二甲基胺基为导向基, 在 Pd 作催化剂的条件下, 实现了苄胺邻位的 C(sp 2 )-H 与芳基碘代物的交叉偶联反应. 基于以上工作, Dixon 课题组 [27] 对导向基团进行修饰, 使用含氮杂环作为导向基团, 实现了苄胺衍生物与芳基硼酸酯的偶联反应(Eq. 10).…”

Section: C(sp 2 )-H 键与 C(sp 3 )-M 的偶联反应unclassified

Cross-Coupling of Directed C-H and Organometallic Reagents for C-C Bond Formation

李桦¹,

任相伟²,

赵温涛³

et al. 2017

Chin. J. Org. Chem.

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Transition metal-catalyzed C-H activation is one of the most important areas in organic synthesis. Directed C-H activation can obviate the prefunctionalization of substrate, therefore providing a highly efficient and concise strategy for CC formation. The cross-coupling of transition metal-activated C-H bond with organic electrophilic reagents has been proven effective for construction of various CC bonds. Meanwhile, the oxidative coupling between the corresponding intermediates with organometallic reagents has become the focus for chemists due to their high reactivity, and notable achievements have been made in recent years. Here the oxidative couplings of C-H bond and organometallic reagents have been discussed and summarized according to the hybridization of substrate and organometallic reagents.

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Section: C(sp 2 )-H 键与 C(sp 3 )-M 的偶联反应unclassified

Cross-Coupling of Directed C-H and Organometallic Reagents for C-C Bond Formation

李桦¹,

任相伟²,

赵温涛³

et al. 2017

Chin. J. Org. Chem.

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“…Palladium catalyzed C–H functionalization is particularly suited to meet this need as the amine, or protected version thereof, can coordinate with a palladium catalyst and direct the functionalization of a designated C–H bond that is within an appropriate distance. Indeed, free amino groups, 2 as well as a variety of modified directing groups, 3 have been used to direct transition metal catalysts to ortho -C–H bonds which are proximal to the amino group. 4 However, methods which functionalize the distal C–H bonds of these substrates are still somewhat rare.…”

Section: Introductionmentioning

confidence: 99%

Ligand-Enabled meta-Selective C–H Arylation of Nosyl-Protected Phenethylamines, Benzylamines, and 2-Aryl Anilines

et al. 2016

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A Pd-catalyzed, meta-selective C−H arylation of nosyl-protected phenethylamines, and benzylamines is disclosed using a combination of norbornene and pyridine-based ligands. Subjecting 2-aryl anilines to this protocol lead to meta-C–H arylation at the remote aryl ring. A diverse range of aryl iodides are tolerated in this reaction, along with select heteroaryl iodides. Select aryl bromides bearing ortho-coordinating groups can also be utilized as effective coupling partners in this reaction. The use of pyridine ligands has allowed the palladium loading to be reduced to 2.5 mol%. Furthermore, a catalytic amount of 2-norbornene (20 mol%) to mediate this meta-C–H activation process is demonstrated for the first time. Utilization of a common protecting group as the directing group for meta-C–H activation of amines is an important feature of this reaction in terms of practical applications.

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“…Based on the above results and pioneering studies,3f,g,h, 5a, 16, 18d, 22 the mechanism of acetoxime‐directed ortho ‐arylation reaction is proposed as depicted in Scheme .To begin with, the Pd II species A , which is bound by amino acid ligand, coordinates with the substrate 1 and subsequently activates the ortho ‐CH bond, forming a six‐membered exo ‐palladacycle intermediate B 14. Transmetalation with Ar‐BPin 2 produces intermediate C ,18d, 3h followed by reductive elimination, releases the target molecule 3 , with concomitant generation of Pd 0 species D .…”

Section: Resultsmentioning

confidence: 82%

Palladium(II)‐Catalyzed Acetoxime Directed ortho‐Arylation of Aromatic Alcohols

Guo

Chen

Zhang

et al. 2015

Chemistry A European J

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Biaryls, which contained a benzyloxy motif, were directly constructed through a ligand-promoted Pd(II) -catalyzed ortho-arylation of masked aromatic alcohols. A variety of acetoxime ethers could be coupled with a diverse range of arylboronic acid pinocol esters, giving direct access to bioactive biaryls in modest to good yield. Not only could acetoxime be subsequently removed without a separation, functionalized hydroxylamine derivatives could also be obtained.

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Palladium(ii)-catalysed ortho-arylation of N-benzylpiperidines

Cited by 27 publications

References 43 publications

Cross-Coupling of Directed C-H and Organometallic Reagents for C-C Bond Formation

Cross-Coupling of Directed C-H and Organometallic Reagents for C-C Bond Formation

Ligand-Enabled meta-Selective C–H Arylation of Nosyl-Protected Phenethylamines, Benzylamines, and 2-Aryl Anilines

Palladium(II)‐Catalyzed Acetoxime Directed ortho‐Arylation of Aromatic Alcohols

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