Rh(III)-Catalyzed Selective Coupling of <i>N</i>-Methoxy-1<i>H</i>-indole-1-carboxamides and Aryl Boronic Acids

Zheng, Jing; Zhang, Yan; Cui, Sunliang

doi:10.1021/ol5014312

Cited by 104 publications

(47 citation statements)

References 68 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Thea rylation of indole at the C2position with arylboronic acid was accomplished, aided by an N-methoxy amide as adirecting group. [225] Asummary of the reactions is presented in Table 1.…”

Section: Indole and Its Derivativesmentioning

confidence: 99%

“…However,the majority of studies related to the C7-functionalization of indole have involved converting the indole 193 into the indoline derivative 199.I nt his case,t he reduction of indole was initially performed followed by selective C À Hf unctionalization and then oxidation to provide the target functionalized indole derivative (Scheme 61). [216] (alkenylation) 2013, Li and Wang [217] (alkenylation) 2012, Li [218] (acylation) 2013, Zhou and Li [219] (alkylation) 2012, Zhou and Li [220] (amination) 2014, Xu [221] (cyanation) 2015, Sharma and Vander Eycken [222] (carboxamidation) 2016, Wang and Wang [223] (alkylation) 2016, Li [224] (alkyne insertion) 2014, Cui [225] (arylation) Scheme 60. Rh III -catalyzed C7-alkenylation of indole derivatives with olefins.…”

Section: Indole and Its Derivativesmentioning

confidence: 99%

See 1 more Smart Citation

Rhodium‐Catalyzed C(sp²)‐ or C(sp³)−H Bond Functionalization Assisted by Removable Directing Groups

2019

View full text Add to dashboard Cite

In recent years, transition‐metal‐catalyzed C−H activation has become a key strategy in the field of organic synthesis. Rhodium complexes are widely used as catalysts in a variety of C−H functionalization reactions because of their high reactivity and selectivity. The availability of a number of rhodium complexes in various oxidation states enables diverse reaction patterns to be obtained. Regioselectivity, an important issue in C−H activation chemistry, can be accomplished by using a directing group to assist the reaction. However, to obtain the target functionalized compounds, it is also necessary to use a directing group that can be easily removed. A wide range of directed C−H functionalization reactions catalyzed by rhodium complexes have been reported to date. In this Review, we discuss Rh‐catalyzed C−H functionalization reactions that are aided by the use of a removable directing group such as phenol, amine, aldehyde, ketones, ester, acid, sulfonic acid, and N‐heteroaromatic derivatives.

show abstract

“…Thea rylation of indole at the C2position with arylboronic acid was accomplished, aided by an N-methoxy amide as adirecting group. [225] Asummary of the reactions is presented in Table 1.…”

Section: Indole and Its Derivativesmentioning

confidence: 99%

Section: Indole and Its Derivativesmentioning

confidence: 99%

Rhodium‐Catalyzed C(sp²)‐ or C(sp³)−H Bond Functionalization Assisted by Removable Directing Groups

2019

View full text Add to dashboard Cite

show abstract

“…In 2014, our group reported that N-methoxy indole-Ncarboxamides 81 and aryl boronic acids 82 could selectively transform to different products via slightly changing reaction conditions (Scheme 21). [30] By using 2 mol % [Cp*RhCl 2 ] 2 as catalyst, 4 equivalents of Cu(OAc) 2 as oxidant and MeOH as solvent, the 2-aryl indole derivatives 83 formed via CÀ H activation at 60°C in good yields. Replacing Cu(OAc) 2 by 4 equivalents of Ag 2 O could promote a CÀ H activation/ [4 + 2] cyclization to deliver indole derived heterocycles 84 smoothly.…”

Section: Reaction Of Indole-n-carboxamides With Other Compoundsmentioning

confidence: 99%

Indole‐N‐Carboxylic Acids and Indole‐N‐Carboxamides in Organic Synthesis

Zeng

Lin

Cui

2020

Chemistry An Asian Journal

Self Cite

View full text Add to dashboard Cite

Indoles are ubiquitous structures that are found in natural products and biologically active molecules. The synthesis of indoles and indole‐involved synthetic methodologies in organic chemistry have been receiving considerable attention. Indole‐N‐carboxylic acids and derived indole‐N‐carboxamides are intriguing compounds, which have been widely used in organic synthesis, especially in multicomponent reactions and C−H functionalization of indoles. This Minireview summarizes the advances of reactions involving indole‐N‐carboxylic acids and indole‐N‐carboxamides in organic chemistry, and discusses the synthetic potential and perspective of this field.

show abstract

“…By switching the external oxidant, they were able to obtain either 2-arylated product or subsequently cyclized product (Scheme 48). [63] …”

Section: Rhodium Catalysismentioning

confidence: 99%

A Simple and Versatile Amide Directing Group for C−H Functionalizations

et al. 2016

View full text Add to dashboard Cite

Achieving selective C–H activation at a single and strategic site in the presence of multiple C–H bonds can provide a powerful and generally useful retrosynthetic disconnection. In this context, the directing group serves as a compass to guide the transition metal to C–H bonds using distance and geometry as powerful recognition parameters to distinguish between proximal and distal C–H bonds. However, the installation and removal of directing groups is a practical drawback. To improve the utility of this approach, one can seek solutions in three directions. First, simplifying the directing group; Second, use of common functional groups or protecting groups as directing groups; Third, attaching the directing group to substrates via a transient covalent bond to render directing groups catalytic. This review describes the rational development of an extremely simple and yet broadly applicable directing group for Pd(II), Rh(III) and Ru(II) catalysts, namely, the N-methoxy amide (CONHOMe). Through collective efforts in the community, a wide range of C–H activation transformations using this type of simple directing groups has been developed.

show abstract

Rh(III)-Catalyzed Selective Coupling of N-Methoxy-1H-indole-1-carboxamides and Aryl Boronic Acids

Cited by 104 publications

References 68 publications

Rhodium‐Catalyzed C(sp²)‐ or C(sp³)−H Bond Functionalization Assisted by Removable Directing Groups

Rhodium‐Catalyzed C(sp²)‐ or C(sp³)−H Bond Functionalization Assisted by Removable Directing Groups

Indole‐N‐Carboxylic Acids and Indole‐N‐Carboxamides in Organic Synthesis

A Simple and Versatile Amide Directing Group for C−H Functionalizations

Contact Info

Product

Resources

About

Rh(III)-Catalyzed Selective Coupling of N-Methoxy-1H-indole-1-carboxamides and Aryl Boronic Acids

Cited by 104 publications

References 68 publications

Rhodium‐Catalyzed C(sp2)‐ or C(sp3)−H Bond Functionalization Assisted by Removable Directing Groups

Rhodium‐Catalyzed C(sp2)‐ or C(sp3)−H Bond Functionalization Assisted by Removable Directing Groups

Indole‐N‐Carboxylic Acids and Indole‐N‐Carboxamides in Organic Synthesis

A Simple and Versatile Amide Directing Group for C−H Functionalizations

Contact Info

Product

Resources

About

Rhodium‐Catalyzed C(sp²)‐ or C(sp³)−H Bond Functionalization Assisted by Removable Directing Groups

Rhodium‐Catalyzed C(sp²)‐ or C(sp³)−H Bond Functionalization Assisted by Removable Directing Groups