71277-10-6Relevant articles and documents
Tandem oxidation-dehydrogenation of (hetero)arylated primary alcohols via perruthenate catalysis
Bettencourt, Christian J.,Chow, Sharon,Moore, Peter W.,Read, Christopher D.G.,Jiao, Yanxiao,Bakker, Jan Peter,Zhao, Sheng,Bernhardt, Paul V.,Williams, Craig M.
, p. 652 - 659 (2021/09/08)
Tandem oxidative-dehydrogenation of primary alcohols to give a,b-unsaturated aldehydes in one pot are rare transformations in organic synthesis, with only two methods currently available. Reported herein is a novel method using the bench-stable salt methyltriphenylphosphonium perruthenate (MTP3), and a new co-oxidant NEMO&middoPF6 (NEMO = N-ethyl-N-hydroxymorpholinium) which provides unsaturated aldehydes in low to moderate yields. The Ley-Griffith oxidation of (hetero)arylated primary alcohols with N-oxide co-oxidants NMO (NMO = N-methylmorpholine N-oxide)/NEMO, is expanded by addition of the N-oxide salt NEMO&middoPF6 to convert the intermediate saturated aldehyde into its unsaturated counterpart. The discovery, method development, reaction scope, and associated challenges of this method are highlighted. The conceptual value of late-stage dehydrogenation in natural product synthesis is demonstrated via the synthesis of a polyene scaffold related to auxarconjugatin B.
Iron-facilitated direct oxidative C-H transformation of allyl arenes to alkenyl aldehydes
Wang, Teng,Xiang, Shi-Kai,Qin, Chong,Ma, Jun-An,Zhang, Li-He,Jiao, Ning
supporting information; experimental part, p. 3208 - 3211 (2011/06/28)
A direct oxidative approach to alkenyl aldehydes from allyl arenes via allyl sp3 C-H functionalization was disclosed. An inexpensive iron catalyst was employed to facilitate this transformation. The mechanistic studies indicate that the cleavage of the allyl sp3 C-H bond is involved in the rate-determining step.
