Hydroxyamination of aryl C–H bonds with N-hydroxycarbamate by synergistic Rh/Cu catalysis at room temperature

Yang, Wei; Sun, Jiaqiong; Xu, Xianxiu; Zhang, Qian; Li, Qun

doi:10.1039/c3cc49496a

Cited by 39 publications

(20 citation statements)

References 40 publications

(10 reference statements)

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“…This nitroso product was already detected by HRMS. Moreover, its presence was further confirmed by trapping with 1,3-cyclohexadiene [18] (Scheme 6 a). The nitrone [D 6 ]1 a and 2 a were then subjected to the standard reaction conditions A, and 1 H NMR analysis of the isolated product revealed significant H/D exchange only at the 5-position (Scheme 6 b), thus indicative of reversibility of the C À H activation process.…”

Section: Nitrone Directing Groups In Rhodium(iii)-catalyzed C à H Actmentioning

confidence: 55%

Nitrone Directing Groups in Rhodium(III)‐Catalyzed C−H Activation of Arenes: 1,3‐Dipoles versus Traceless Directing Groups

Xie

et al. 2016

Angew Chem Int Ed

124

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Functionalizable directing groups (DGs) are highly desirable in C-H activation chemistry. The nitrone DGs are explored in rhodium(III)-catalyzed C-H activation of arenes and couplings with cyclopropenones. N-tert-butyl nitrones bearing a small ortho substituent coupled to afford 1-naphthols, where the nitrone acts as a traceless DG. In contrast, coupling of N-tert-butyl nitrones bearing a bulky ortho group follows a C-H acylation/[3+2] dipolar addition pathway to give bicyclics. The coupling of N-arylnitrones follows the same acylation/[3+2] addition process but delivers different bicyclics.

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Section: Nitrone Directing Groups In Rhodium(iii)-catalyzed C à H Actmentioning

confidence: 55%

Nitrone Directing Groups in Rhodium(III)‐Catalyzed C−H Activation of Arenes: 1,3‐Dipoles versus Traceless Directing Groups

Xie

et al. 2016

Angew Chem Int Ed

124

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“…[72] It was found 10 mol% of CuCl was essential for the reaction to proceed. They speculated that the Cu(I)-catalyzed oxidation of the N-hydroxycarbamate to the nitrosocarbonyl compound which then acted as an electrophile and reacted with the rhodacycle derived from Rh(III)-catalyzed C(sp 2 )–H activation.…”

Section: Rhodium Catalysismentioning

confidence: 99%

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

et al. 2016

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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.

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“…28 Copper catalysts have been used with cesium acetate as well to perform intramolecular amination 29 and intramolecular hydroxyamination. 30 Perkin Synthesis. This synthesis is a well-known organic reaction yielding cinnamic acid from an aromatic aldehyde and an anhydride.…”

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confidence: 99%

Cesium Acetate

Yode

2015

Encyclopedia of Reagents for Organic Synthesis

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Hydroxyamination of aryl C–H bonds with N-hydroxycarbamate by synergistic Rh/Cu catalysis at room temperature

Cited by 39 publications

References 40 publications

Nitrone Directing Groups in Rhodium(III)‐Catalyzed C−H Activation of Arenes: 1,3‐Dipoles versus Traceless Directing Groups

Nitrone Directing Groups in Rhodium(III)‐Catalyzed C−H Activation of Arenes: 1,3‐Dipoles versus Traceless Directing Groups

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

Cesium Acetate

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