A selective, practical and scalable aerobic oxidation of alcohols is described using catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and HNO 3 , with molecular oxygen serving as the terminal oxidant. The method was successfully applied to the oxidation of a wide range of benzylic, propargylic and allylic alcohols, including two natural products, namely carveol and podophyllotoxin. The conditions are also applicable to the selective oxidative deprotection of PMB ethers.

A copper-catalyzed borylation of allylic nitroalkanes is reported. The method, which exploits the high versatility of the nitroalkane precursors, tolerates a variety of functional groups and allows a straightforward access to diversely substituted allylboronic esters in high yields. This unprecedented reactivity towards copper complexes has been further exploited in the synthesis of a number of γ fluoroallyl boronic esters starting from readily available α fluoroallyl nitroalkanes, as well as in various post-functionalizations towards synthetically useful building blocks. Both the reaction mechanism and the chemoselectivity have been rationalized experimentally and through DFT calculations.