Oxidative acylation of α,α‐diarylallylic alcohols: Synthesis of 1,2,4‐triarylbutane‐1,4‐diones

Abstract

A metal‐free mediated oxidative acylation of α,α‐diarylallylic alcohols with simple aromatic aldehydes for the synthesis of 1,2,4‐triphenylbutane‐1,4‐diones is presented. In the presence of TBPB (tert‐butyl peroxybenzoate), desired products were obtained in good to excellent yields for 28 examples. This protocol features high regioselectivity, wide functional group tolerance and atom economy.

Oxidative thiocyanation of allylic alcohols: an easy access to allylic thiocyanates with K2S2O8 and NH4SCN

“…Aryl allylic alcohols have been well studied as powerful molecular scaffolds to realize alkene difunctionalization via a domino radical addition and aryl migration process. Various types of radicals including trifluoromethyl, 21 alkyl, 22 ketyl, 23 halogen, 24 and phosphorus 25 were introduced into the double bond with concomitant ipso aryl migration to deliver α-aryl-β-substituted ketones (Scheme 2a). Inspired by these seminal works and our interest in organic thiocyanates, 20 d , e we envisioned that a thiocyanate radical might be able to engage in these cascade reactions to generate α-aryl-β-thiocyano ketones.…”