The Fischer Indole Synthesis.

Robinson, B.

doi:10.1021/cr60224a003

Cited by 519 publications

(239 citation statements)

References 119 publications

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“…[160] In 1998 Buchwald showed that N-aryl benzophenone hydrazones could be made by palladium-catalyzed amination of aryl bromides using the chelating phosphines BINAP or Xantphos and that these intermediates could participate in Fischer indolization (Scheme 15). [161,162] This process has subsequently been extended to aryl chlorides by the application of dialkylbiaryl phosphine ligands [163] and has been studied in detail on a larger scale by workers at Rhodia.…”

Section: Applications In the Construction Of Heterocyclesmentioning

confidence: 99%

Biaryl Phosphane Ligands in Palladium‐Catalyzed Amination

2008

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Palladium-catalyzed amination of aryl halides has undergone rapid development in the last 12 years. This has been largely driven by implementation of new classes of ligands. Biaryl phosphines have proven to provide especially active catalysts in this context. This review discusses the applications that these catalysts have found in C-N cross-coupling in heterocycle synthesis, pharmaceuticals, materials science and natural product synthesis.

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Section: Applications In the Construction Of Heterocyclesmentioning

confidence: 99%

Biaryl Phosphane Ligands in Palladium‐Catalyzed Amination

2008

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“…4,5 As a first approach, we attempted to prepare 5 by the standard Fischer indole synthesis. 6 Reaction of 3,4-difluoroaniline according to Japp-Klingemann method 7 furnished the 3,4-difluorophenyl hydrazone of ethyl pyruvate 7, which was converted to a mixture of 5 and 6 by heating with polyphosphoric acid (PPA) 8 (Scheme 1). The isomeric mixture was separated by repeated passages on chromatography column to afford pure 5 (15%) and 6 (22%).…”

Section: Resultsmentioning

confidence: 99%

Synthetic approaches to difluoroindolecarboxylic acid ethyl esters

Silvestri¹,

Artico²,

Regina³

et al. 2003

Arkivoc

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Synthetic approaches to ethyl 4,5-difluoroindole-2-carboxylate and ethyl 5,6-difluoroindole-2-carboxylate by Fischer indole synthesis and by the reaction of lithiated N-BOC-3,4-difluoro-2-methylaniline with diethyl oxalate or ethyl bromopyruvate were investigated. A simple and direct preparation of ethyl 4,5-difluoroindole-3-carboxylate from lithiated N-BOC-3,4-difluoroaniline and ethyl bromopyruvate was found.

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“…9 It is striking that the above result was achieved for a reaction, such as the Fischer indole synthesis 10 known for more than a century, and to which an entire book has been devoted. 11 In addition to statistical orthogonality, PPs derived from PCA multivariate characterizations have the advantage of being less influenced by measurement errors and system-specific variations than are single descriptors. Moreover, reliable PPs can be obtained from original data matrices even with missing data.…”

Section: Introductionmentioning

confidence: 99%