RhIII‐Catalyzed C–H Allylation of Amides and Domino Cycling Synthesis of 3,4‐Dihydroisoquinolin‐1(2H)‐ones with N‐Bromosuccinimide

Dai, Huimin; Yu, Cao; Lu, Changsheng; Yan, Hong

doi:10.1002/ejoc.201501551

Cited by 33 publications

(13 citation statements)

References 86 publications

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“…13 ), and a carprofen derivative (Fig. 3 ) 63 , 64 , which is a non-steroidal anti-inflammatory drug. Because of the possible decomposition of carprofen protected with pivaloyl amide in the reaction, a relatively low yield of 7 was afforded.…”

Section: Resultsmentioning

confidence: 99%

Ruthenium(II)-enabled para-selective C–H difluoromethylation of anilides and their derivatives

et al. 2018

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Transition-metal-catalyzed direct site-selective functionalization of arene C–H bonds has emerged as an innovative approach for building the core structure of pharmaceutical agents and other versatile complex compounds. However, para-selective C–H functionalization has seldom been explored, only a few examples, such as steric-hindered arenes, electron-rich arenes, and substrates with a directing group, have been reported to date. Here we describe the development of a ruthenium-enabled para-selective C–H difluoromethylation of anilides, indolines, and tetrahydroquinolines. This reaction tolerates various substituted arenes, affording para-difluoromethylation products in moderate to good yields. Results of a preliminary study of the mechanism indicate that chelation-assisted cycloruthenation might play a role in the selective activation of para-CAr–H bonds. Furthermore, this method provides a direct approach for the synthesis of fluorinated drug derivatives, which has important application for drug discovery and development.

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Section: Resultsmentioning

confidence: 99%

Ruthenium(II)-enabled para-selective C–H difluoromethylation of anilides and their derivatives

et al. 2018

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“…Another allylation procedure was reported by Yan, this time using allyl bromides and a Rh catalyst ( Scheme 24B ), which made the procedure less attractive but the advantage was the commercial availability of the Rh catalyst, which is unfortunately not yet the case for many Co species. 194 Additionally, the reaction was carried out at room temperature. Yields were in a preparatively useful range (34–93%) but in this case also di-allylated products were formed.…”

Section: Monodentate Amides As Dgs In C–h Functionalisation Reactionsmentioning

confidence: 99%

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

et al. 2018

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“…A palladium‐catalyzed version for n‐butyl ation gave rise to very poor results (12 % yield) and a rhodium‐catalyzed methylation employing MeBF 3 K as a more benign alkylating agent was reported too (43 % yield) . The same site‐selectivity was observed with allylbromides under rhodium catalysis . Moreover, N ‐substituted maleimides were found to be appropriate partners leading to alkylated products upon a formal hydroarylation via ruthenium catalysis as it was shown by Prabhu and co‐workers (Scheme ) .…”

Section: C−c Bond‐forming Reactionsmentioning

confidence: 78%

Steering Site‐Selectivity in Transition Metal‐Catalyzed C−H Bond Functionalization: the Challenge of Benzanilides

Gramage‐Doria

2020

Chemistry A European J

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SelectiveC ÀHb ond functionalization catalyzed by metal complexes have completely revolutionized the wayi n which chemical synthesis is conceived nowadays. Typically, the reactivityo fat ransitionm etal catalyst is the key to control the site-, regio-and/or stereo-selectivity of aC ÀHb ond functionalization. Of particulari nterests are molecules that contain multiple CÀHb onds prone to undergo CÀHb ond activations with very similar bond dissociation energies at different positions. This is the case of benzanilides, relevant chemical motifs that are found in many useful fine chemicals, in which two CÀHs ites are present in chemically different aromatic fragments. In the last years, it has been found that depending on the metal catalyst and the reaction conditions, the amide motif might behave as ad irecting group towardst he metal-catalyzed CÀHb ond activation in the benzamide site or in the anilides ite. The impact and the consequences of such subtle control of site-selectivity are herein reviewed with important applicationsi ncarboncarbon and carbon-heteroatomb ond forming processes. The mechanisms unraveling these unique transformations are discussed in order to provide ab etter understanding for future developmentsi nt he field of site-selective CÀHb ond functionalization with transition metal catalysts.

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Rh^III‐Catalyzed C–H Allylation of Amides and Domino Cycling Synthesis of 3,4‐Dihydroisoquinolin‐1(2H)‐ones with N‐Bromosuccinimide

Cited by 33 publications

References 86 publications

Ruthenium(II)-enabled para-selective C–H difluoromethylation of anilides and their derivatives

Ruthenium(II)-enabled para-selective C–H difluoromethylation of anilides and their derivatives

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

Steering Site‐Selectivity in Transition Metal‐Catalyzed C−H Bond Functionalization: the Challenge of Benzanilides

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