Direct carboxamidation of indoles by palladium-catalyzed C–H activation and isocyanide insertion

Peng, Jinfang; Liu, Lanying; Hu, Ziwei; Huang, Jinbo; Zhu, Qiang

doi:10.1039/c2cc30351e

Cited by 108 publications

(41 citation statements)

References 44 publications

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“…146 Indole-3-carboxamides 250 could be obtained in good yields by using Cu(OAc) 2 as an oxidant in conjunction with TFA and water as additives, which were crucial for preventing the formation of undesired side products. Functionalized indoles with electron-withdrawing or donating groups placed about the aromatic ring were effective coupling partners.…”

Section: Isocyanidesmentioning

confidence: 99%

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

2016

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The transition metal-catalyzed addition of C–H bonds to carbonyls, imines and related polarized π-bonds has emerged as a particularly efficient and powerful approach for the construction of an incredibly diverse array of heteroatom substituted products. Readily available and stable inputs are typically employed, and reactions often proceed with very high functionality group compatibility and without the production of waste byproducts. Additionally, many transition metal-catalyzed C–H bond additions to polarized π-bonds occur within cascade reaction sequences to provide rapid access to a diverse array of different heterocyclic as well as carbocyclic products. This review highlights the diversity of transformations that have been achieved, catalysts that have been used, and types of products that have been prepared through the transition metal catalyzed addition of C–H bonds to carbonyls, imines and related polarized π-bonds.

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Section: Isocyanidesmentioning

confidence: 99%

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

2016

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“…Reaction Couplingpartner/reagentC atalyst References 1a rylation aryl halides Pd [101,102,104,105] 2b enzoic acids Pd [107] 3a rylhydrazines Pd [108] 4c yclohexanones Pd [109] 5d iaryliodonium salts Cu [110] 6N -heterocyclic compounds Pd [111][112][113][114] 7a lkynylation alkynes Au [115] 8b enzylation benzylic alcohols Au [116] 9o lefination alkenes Pd [117,118] 10 acylation benzaldehydes Pd [119] 11 TMEDA Cu [120] 12 nitrilesP d [121] 13 CO and alcohols Rh [122] 14 a-amino carbonyl compounds Cu [123] 15 Pd [124] 16 synthesis of bisindoles alcohols Pd [141,142] 17 aldehydes Ag [143] 18 amines Pd [144] 19 annulation alkenes Pd 21 cyanation CuCN Pd [150] 22 K 4 [Fe(CN) 6 ]P d [151] 23 t-BuNC Pd [152] 24 NH 4 HCO 3 and DMSOP d [153] 25 amidation isocyanides Pd [154] Scheme 44. Pd-catalyzedarylation.…”

Section: Entrymentioning

confidence: 99%

“…[153] Amidation at the C-3p osition of indolesh aveb een achieved by employing isonitrilesa sc oupling partners,( Scheme 71). [154] Thep rocess involved Pd-cata- lyzed C À Ha ctivation andi socyanide insertion to furnish carboxamidated indolesi ng ood to excellent yields.…”

Section: Introduction Of Groups Containing Nitrogenmentioning

confidence: 99%

Transition Metal‐Catalyzed CH Activation of Indoles

2015

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Thel ast decades have seen at remendous expanse in the applicationo fC À Ha ctivation of many different substrate classes,including the invaluable indole scaffold. Following the exciting emergence of C À Ha ctivation as am ulti-faceted platform for functionalization, av ersatile toolb ox has been developed for the preparation of structurally diverse indoles. This review article discussesr ecent advances and strategies for transitionm etal-catalyzed C À Ha ctivationofi ndoles.

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“…(108)]. [153] Unprotected or N -alkyl-substituted indoles 494 work equally well in reactions with tert -butyl, isopropyl, cyclohexyl, adamantyl, and 2,6-dimethylphenyl isonitriles. Indoles protected with electron-withdrawing groups do not react.…”

Section: Urea Amide and Amidine Synthesesmentioning

confidence: 99%

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

et al. 2014

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Isonitriles are delicately poised chemical entities capable of being coaxed to react as nucleophiles or electrophiles. Directing this tunable reactivity with metal and non-metal catalysts provides rapid access to a large array of complex nitrogenous structures ideally functionalized for medicinal applications. Isonitrile insertion into transition metal complexes has featured in numerous synthetic and mechanistic studies, leading to rapid deployment of isonitriles in numerous catalytic processes, including multicomponent reactions (MCR). Covering the literature from 1990–2014, the present review collates reaction types to highlight reactivity trends and allow catalyst comparison.

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Direct carboxamidation of indoles by palladium-catalyzed C–H activation and isocyanide insertion

Abstract: A selective C3 carboxamidation of indoles including free (N-H) ones by palladium-catalyzed sequential C-H activation-isocyanide insertion has been developed.

Cited by 108 publications

References 44 publications

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

Transition-Metal-Catalyzed C–H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds

Transition Metal‐Catalyzed CH Activation of Indoles

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

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