Palladium-catalyzed C2-acylation of indoles with aryl and alkyl aldehydes

Yan, Xiao‐Biao; Shen, Yuemao; Chen, Daoqian; Gao, Pin; Li, Ying-Xiu; Song, Xian‐Rong; Liu, Xueyuan; Liang, Yong‐Min

doi:10.1016/j.tet.2014.08.025

Cited by 37 publications

(15 citation statements)

References 45 publications

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“…42 The majority of substrate scope was carried out using the 2-pyridyl directing group, although 2-pyrimidine was also effective. Electron-withdrawing and electron-donating functionalities were well tolerated at nearly every position of the indole ring.…”

Section: Aldehydesmentioning

confidence: 99%

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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: Aldehydesmentioning

confidence: 99%

“…Two related transformations were later published by the laboratories of Liu and Sekar for Pd-catalyzed oxidative C2 acylation of pyridyl- and pyrimidylindoles, respectively (See Section 2.4.1, Scheme 26–27). 42,43 …”

Section: Aldehydesmentioning

confidence: 99%

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

2016

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“…Reaction Coupling partner/reagent Catalyst References 1a rylation aryl halides Rh [25] 2P d [26,27,[31][32][33] 3a renes Pd [28][29][30] 4d iaryliodoniumsalts Pd [33,35] 5a rylboronr eagents Pd [36][37][38] 6R h, Ru [39,40] 7a rylsilanes Rh [41] 8P d [42] 9b enzoic acid Rh [43] 10 alkynylationa lkynes Pd [44] 11 alkenylationP d [46,[50][51][52]54,55] 12 alkenes Rh [48,53,59] 13 Ru [53b,60] 14 vinylcarboxylic acids Rh [61] 15 Ru [49] 16 alkynes Fe [56] 17 Co [58] 18 alkylation alkyl halides Pd [63,65] 19 Co [66] 20 Pd [70] 21 Fe [56] 22 alkenes Ir [67,71] 23 Co [69] 24 Ir [72] 25 acylationa ldehydes Pd [75] 26 Rh [76] 27 annulations Co [57] 28 Pd [77,…”

Section: Entrymentioning

confidence: 99%

“…[75] Them ethod involved the coupling of indolesa nd aldehydest of orm 2-acylindoles and exhibited excellent functional group tolerance.R hc atalysis can also successfully be utilized to achieve similar coupling reactions of indoles and benzaldehydes. [76] Scheme 24.…”

Section: Acylationmentioning

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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“…8 Subsequently, Liang and coworkers described a palladium-catalyzed C2-acylation of indoles with aryl and alkyl aldehydes via C-H functionalization. 9 Very recently, a palladium-catalyzed C2-acylation of N-pyrimidyl indoles with a-diketones 10a and ethyl glyoxylate 10b was reported. Despite the signicant progress made in the area of C2-acylation of indoles, there are no reports on the formation of a C-C bond directly from the more challenging and inert Csp 3 -H bond.…”

Section: Introductionmentioning

confidence: 99%