Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation.
Addition of nitrosobenzene to pinacol allylboronates leads to oxidation of the organoboron with concomitant rearrangement of the substrate alkene. This reaction appears to proceed by allylboration of the nitroso group in analogy to carbonyl and imine allylation reactions. Remarkably, the N-O bond is cleaved during the reaction such that simple alcohols are the final reaction product.
Kyne
Robert E
RE
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Ryan
Michael C
MC
Kliman
Laura T
LT
Morken
James P
JP
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000466:Alkadienes / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D009603:Nitroso Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010545:Peroxides / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D000466:Alkadienes; D000498:Allyl Compounds; D001896:Boron Compounds; D009603:Nitroso Compounds; D010545:Peroxides; C025947:propadiene; C012456:nitrosobenzene