An oxidative cross‐dehydrogenative coupling (CDC) reaction for the formation of CC and CP bonds is disclosed using a catalytic amount of DDQ (10 mol %) under aerobic conditions (see scheme). This unprecedented environmentally benign strategy of using AIBN (10 mol %) and molecular oxygen to regenerate DDQ exhibits a larger substrate scope. For the first time, an efficient utility of 4‐hydroxycoumarins as pronucleophiles for CDC is presented.
A novel non-metal catalyzed oxidation of organic azides to nitriles under solvent-free conditions is presented employing catalytic amounts of KI, and DABCO in aq. TBHP at room temperature. This non-metal catalyzed oxidation of azides provides good selectivity as double and triple bonds were not oxidized under the present reaction conditions.
Synthesis and nontrivial optical resolution of a helicene-like dication, helquat 1, has been accomplished. Starting with gram scale of the racemic helquat 1 sample, Dutch Resolution using family of 3 tartrate anions was key to achieve successful separation of M and P helical enantiomers of 1. Hundreds of milligrams of each enantiomer of this configurationally stable C -symmetric helquat have been obtained. Racemization barrier of 1 has been determined. To our knowledge this is the first report on Dutch Resolution performed with a helicene-like compound. Moreover, there are no literature precedents for Dutch Resolution of chiral quaternary ammonium cations.
Cross dehydrogenative coupling of tetrahydroisoquinolines (I) and (VI) with enolizable ketones (II) and (IV) as well as phosphonates (VII), resp., proceeds efficiently in the presence of catalytic amounts of DDQ and AIBN (10 mol%). Only stoichiometric amounts of phosphonates are necessary. -(ALAGIRI, K.; DEVADIG, P.; PRABHU*, K. R.; Chem. Eur. J. 18 (2012) 17, 5160-5164, http://dx.
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