Wacker-type oxidation of internal alkenes using Pd(Quinox) and TBHP.
The Pd-catalyzed TBHP-mediated Wacker-type oxidation of internal alkenes is reported. The reaction uses 2-(4,5-dihydro-2-oxazolyl)quinoline (Quinox) as ligand and TBHP(aq) as oxidant to deliver single ketone constitutional isomer products in a predictable fashion from electronically biased olefins. This methodology is showcased through its application on an advanced intermediate in the total synthesis of the antimalarial drug artemisinin.
Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA.
Ryan J
RJ
DeLuca
Jennifer L
JL
Edwards
Laura D
LD
Steffens
Brian W
BW
Michel
Xiaoxiao
X
Qiao
Chunyin
C
Zhu
Silas P
SP
Cook
Matthew S
MS
Sigman
D000475:Alkenes / Q000737:chemistry*; D037621:Artemisinins / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry*
C581731:2-(4,5-dihydro-2-oxazolyl)quinoline; D000475:Alkenes; D037621:Artemisinins; D007659:Ketones; D008024:Ligands; D009942:Organometallic Compounds; D010080:Oxazoles; D011804:Quinolines; D010165:Palladium; C031327:artemisinin