Distinct reactivity of Pd(OTs)2: the intermolecular Pd(II)-catalyzed 1,2-carboamination of dienes.
A Pd-catalyzed intermolecular 1,2-carboamination route to indolines from N-aryl ureas and 1,3-dienes that proceeds under mild conditions in relatively nonacidic media, is presented. The in situ generation, or preformation, of a palladium tosylate emerges as a key parameter in gaining the requisite reactivity for the C-H insertion/carbopalladation/nucleophilic displacement process.
Houlden
Chris E
CE
School of Chemistry, Cantock's Close, University of Bristol, Bristol, BS8 1TS, UK.
Bailey
Chris D
CD
Ford
J Gair
JG
Gagné
Michel R
MR
Lloyd-Jones
Guy C
GC
Booker-Milburn
Kevin I
KI
D000586:Amination; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry*; D011090:Polyenes / Q000737:chemistry*; D013449:Sulfonamides; D014050:Toluene / Q000031:analogs & derivatives; D014508:Urea; D000096926:Benzenesulfonamides
D007211:Indoles; D010165:Palladium; D011090:Polyenes; D013449:Sulfonamides; D014050:Toluene; D014508:Urea; C013307:2-toluenesulfonamide; D000096926:Benzenesulfonamides