Oxidation of propargylic alcohols to the corresponding aldehydes and ketones was achieved at room temperature using 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and calcium hypochlorite (Ca(OCl)2). Propargylic diols yielded corresponding dialdehydes as the product. This system was found to be very efficient for both the electron donating and electron withdrawing groups such as methoxy and nitro substituted alcohols, respectively. This method does not require any additives and demonstrates the controlled, selective oxidation of propargylic alcohols affording up to 97% isolated yield.
