First C-H Activation Route to Oxindoles using Copper Catalysis

TY - JOUR

T1 - First C-H Activation Route to Oxindoles using Copper Catalysis

AU - Klein, Johannes E. M. N.

AU - Perry, Alexis

AU - Pugh, David S.

AU - Taylor, Richard J. K.

PY - 2010/8/6

Y1 - 2010/8/6

N2 - The preparation of 3,3-disubstituted oxindoles by a formal C-H, Ar-H coupling of anilides is described. Highly efficient conditions have been Identified using catalytic (5 mol %) Cu(OAc)(2)center dot H2O with atmospheric oxygen as the reoxidant; no additional base is required, and the reaction can be run in toluene or mesitylene. Optimization studies are reported together with a scope and limitation investigation based on variation of the anilide precursors. The application of this methodology to prepare a key Intermediate for the total synthesis of the anticancer, analgesic oxindole alkaloid Horsfiline is also described.

AB - The preparation of 3,3-disubstituted oxindoles by a formal C-H, Ar-H coupling of anilides is described. Highly efficient conditions have been Identified using catalytic (5 mol %) Cu(OAc)(2)center dot H2O with atmospheric oxygen as the reoxidant; no additional base is required, and the reaction can be run in toluene or mesitylene. Optimization studies are reported together with a scope and limitation investigation based on variation of the anilide precursors. The application of this methodology to prepare a key Intermediate for the total synthesis of the anticancer, analgesic oxindole alkaloid Horsfiline is also described.

KW - CARBON BOND FORMATION

KW - INTRAMOLECULAR CYANOAMIDATION

KW - DERIVATIVES

KW - AGENTS

UR - http://www.scopus.com/inward/record.url?scp=77955135659&partnerID=8YFLogxK

U2 - 10.1021/ol1012668

DO - 10.1021/ol1012668

M3 - Article

SN - 1523-7060

VL - 12

SP - 3446

EP - 3449

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -