Jia, YanxingZhu, Jieping2010-11-252010-11-252010-11-25200610.1021/jo061471shttps://infoscience.epfl.ch/handle/20.500.14299/58445One-pot synthesis of indoles by a palladium-catalyzed annulation of o-haloanilines and aldehydes has been developed. Coupling of o-iodoaniline with aldehyde is realized under mild ligandless conditions [Pd(OAc)2, DABCO, DMF, 85 DegC], whereas X-Phos is found to be the ligand of choice for coupling reactions involving o-chloroanilines/o-bromoanilines and aldehydes. A variety of o-haloanilines with different electronic properties are suitable substrates, and aldehydes including chiral ones participated in this reaction without racemization. Coupling of (S)-2-N,N-di-tert-butoxycarbonyl-5-oxopentanoate, derived from L-glutamic acid, with o-haloanilines provides a rapid access to the ring-A-substituted tryptophans in good to excellent yields. [on SciFinder (R)]Amines Role: RCT (Reactant)RACT (Reactant or reagent) (arom.o-halo; palladium-catalyzed modular synthesis of highly functionalized indoles and tryptophans by direct annulation of substituted o-haloanilines and aldehydes); Cyclization; Cyclization catalysts (palladium-catalyzed modular synthesis of highly functionalized indoles and tryptophans by direct annulation of substituted o-haloanilines and aldehydes); Aldehydes Role: RCT (Reactant)RACT (Reactant or reagent) (palladium-catalyzed modular synthesis of highly functionalized indoles and tryptophans by direct annulation of substituted o-haloanilines and aldehydes)indole tryptophan prepn; annulation haloaniline aldehyde palladium catalysttext::journal::journal article::research article