2014
DOI: 10.1002/anie.201410342
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Rhodium(III)‐Catalyzed Cyclative Capture Approach to Diverse 1‐Aminoindoline Derivatives at Room Temperature

Abstract: A Rh(III) -catalyzed C-H activation/cyclative capture approach, involving a nucleophilic addition of C(sp(3) )-Rh species to polarized double bonds is reported. This constitutes the first intermolecular catalytic method to directly access 1-aminoindolines with a broad substituent scope under mild conditions.

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Cited by 148 publications
(55 citation statements)
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“…The synthesis of these compounds generally relies on Pd-or Rh-catalyzed cyclization of alkenes with aryl halides [54] or C-H activation [55]. However, because of the ease of b-hydride elimination (Heck-type reaction) for the alkyl intermediate formed after alkene insertion, these methods often require strongly deactivating alkenes or alkenes bearing no b-hydrogen, thus limiting the utility of this transformation.…”
Section: Miscellaneousmentioning
confidence: 99%
“…The synthesis of these compounds generally relies on Pd-or Rh-catalyzed cyclization of alkenes with aryl halides [54] or C-H activation [55]. However, because of the ease of b-hydride elimination (Heck-type reaction) for the alkyl intermediate formed after alkene insertion, these methods often require strongly deactivating alkenes or alkenes bearing no b-hydrogen, thus limiting the utility of this transformation.…”
Section: Miscellaneousmentioning
confidence: 99%
“…Due to their importance, new synthetic methods are perpetually developed . Recently published strategies comprise the assembly of the indole moiety through cobalt‐, rhodium‐,, or palladium‐catalyzed reactions of such diverse starting materials as nitrones, azo esters, hydrazides,, nitrosoanilines, enamines, or imines . In addition to these developments, the classical Fischer indole synthesis is also constantly improved and remains attractive in medicinal chemistry and in natural products synthesis…”
Section: Methodsmentioning
confidence: 99%
“…However, these examples required stoichiometric external oxidants (or hydrogen acceptors) and/or elevated temperature. Consequently the development of the transition‐metal‐catalyzed oxidative sp 2 CH bond olefination of arenes with unactivated alkenes that proceeds under ambient conditions (at room temperature using air as a terminal oxidant) remains a challenge 16…”
Section: Optimization Of Reaction Conditions For Rhodium‐catalyzed Oxmentioning
confidence: 99%