We describe a palladium catalyzed C7-acetoxylation of indolines {with a|having a|using a} {range|variety} of amide directing groups. {While|Whilst|Although|Even though|When|Though} {a variety of|a number of|many different|various|a range of|several different} substituents are tolerated {on the|around the} indoline-core {and the|and also the|as well as the|along with the|plus the} N1-acyl group, the acetoxylation is most sensitive {to the|towards the|for the} C2- and C6-indoline substituents. The practicality of this indoline C7-acetoxylation is demonstrated {using|utilizing|making use of|employing|working with|applying} a cinnamamide substrate on mmol-scale. {Several|A number of|Numerous|Many|Various|Quite a few} N1-acyl groups, {including|such as|which includes|like} {those|these} present in {natural|all-natural|organic} alkaloids, guide C7-acetoxylation of indoline substrates {over|more than} a competitive C5-oxidation. The application of this chemistry {allowed|permitted} for {the first|the very first|the initial} synthesis of N-benzoylcylindrocarine by late-stage C17-acetoxylation of N-benzoylfendleridine. 4-Aminomethylbenzylalcohol Purity 2-Bromo-N-phenylaniline custom synthesis PMID:25023702
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