Route to 3-Amidino Indoles via Pd(II)-Catalyzed C–H Bond Activation

Rydfjord, Jonas; Skillinghaug, Bobo; Brandt, Peter; Odell, Luke R.; Larhed, Mats

doi:10.1021/acs.orglett.7b01836

Cited by 10 publications

(3 citation statements)

References 41 publications

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“…First, the undesired C3 position of the indole ring can undergo innate C–H functionalization. Second, the carboxamide moiety may confiscate the Pd catalyst through robust coordination . In continuation of our interest in Pd-catalyzed C–H activation reactions of C 60 , herein we report the first Pd catalytic system for the C–H activation reaction of N -methoxy-1 H -indole-1-carboxamides with C 60 under mild reaction conditions.…”

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confidence: 98%

Palladium-Catalyzed Heteroannulation of Indole-1-carboxamides with [60]Fullerene and Subsequent Electrochemical Transformations

et al. 2019

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A highly efficient heteroannulation between [60]fullerene (C60) and N-methoxy-1H-indole-1-carboxamides has been successfully achieved via the palladium-catalyzed C–H activation and subsequent cyclization. This protocol has remarkable functional group tolerance for the synthesis of C60-fused 3,4-dihydropyrimido[1,6-a]indol-1(2H)-ones. Furthermore, the electrochemically generated dianionic C60-fused 3,4-dihydropyrimido[1,6-a]indol-1(2H)-ones can be regioselectively transformed into 1,2,3,4-, 1,2,3,16-, and 1,4,9,25-adducts of C60.

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confidence: 98%

Palladium-Catalyzed Heteroannulation of Indole-1-carboxamides with [60]Fullerene and Subsequent Electrochemical Transformations

et al. 2019

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“…Pd(II)-catalyzed C-H bond activation of the indole (Scheme 14). 21 Notably, the superior catalytic efficiency of this reaction was obtained by using the Pd(II)/4,5-diazafluoren-9one (DAF) ligand system, instead of well-known Pd(II)/bidentate nitrogen ligands. Under the optimized reaction conditions [Pd(TFA) 2 /DAF, PTSA, DMA, 100 °C), both N-methylindoles and free NH-indoles reacted with various N-disubstituted cyanamides to afford the corresponding 3amidino indoles 8 in reasonable yields.…”

Section: Short Review Synthesismentioning

confidence: 99%

Recent Advances in Transition-Metal-Catalyzed C–H Addition to Nitriles

Cui

Liao

2021

Synthesis

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Transition-metal-catalyzed C–H bond addition to nitriles has emerged as a powerful synthetic approach for the construction of C–C bonds in organic synthesis. Due to the merits of atom- and step-economy, as well the easy availability of the starting materials, these transformations not only deliver acyclic aryl ketone products with nitriles as C-building blocks, but can also be utilized for the highly efficient assembly of azaheterocyclic skeletons using nitriles as C–N building blocks. This short review summarizes recent progress on transition-metal-catalyzed C–C bond-forming reactions based on C(sp2)–H and C(sp3)–H additions to nitriles.1 Introduction2 Palladium-Catalyzed C–H Addition to Nitriles2.1 Palladium-Catalyzed C–H Addition to Nitriles for the Preparation of Ketone (Imine) Products2.2 Palladium-Catalyzed C–H Addition to Nitriles for the Preparation of Azaheterocycles2.3 Palladium-Catalyzed C–H Addition to Nitriles/1,2-Rearangement3 Other Transition-Metal-Catalyzed C–H Additions to Nitriles4 Summary and Outlook

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“…Cyanamides have also been demonstrated to be unique building blocks that can participate in an impressive and ever-growing number of transformations involving either the “amino” or the “cyano” groups, or even both. , They are, in addition, excellent candidates for coordination chemistry, notably due to their complexation and bridging properties. , …”

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confidence: 99%

Copper-Catalyzed Alkenylation of Cyanamides

2017

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An efficient procedure for the copper-catalyzed cross-coupling between a broad range of cyanamides and iodoalkenes is reported. Upon reaction with catalytic amounts of copper(I) iodide and 2,2'-bisimidazole in the presence of cesium carbonate in DMF at 80 °C, a fast, regioselective, and stereoretentive cross-coupling occurs. This reaction, which was found to have a broad substrate scope, provides the first general entry to N-alkenylcyanamides, building blocks that hold great synthetic potential.

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Route to 3-Amidino Indoles via Pd(II)-Catalyzed C–H Bond Activation

Cited by 10 publications

References 41 publications

Palladium-Catalyzed Heteroannulation of Indole-1-carboxamides with [60]Fullerene and Subsequent Electrochemical Transformations

Palladium-Catalyzed Heteroannulation of Indole-1-carboxamides with [60]Fullerene and Subsequent Electrochemical Transformations

Recent Advances in Transition-Metal-Catalyzed C–H Addition to Nitriles

Copper-Catalyzed Alkenylation of Cyanamides

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