o-Acetoxylation of oxo-benzoxazines via C–H activation by palladium(ii)/aluminium oxide

Abstract

Direct activation of sp2 C–H bonds by a palladium catalyst has received significant attention in organic chemistry.

FeCl2‐Catalyzed Rearrangement of Aryl Peroxyoxindole into 1,3‐Benzooxazin‐4‐One

“…This intermediate (2 t) is subsequently brominated according to the literature method to afford elastage inhibitor. [11] Moreover, a gram scale reaction was performed with 10 mmol of 1 a using the optimized reaction condition, affording 79% (1.8 g) of 2 a (Scheme 2B).…”

“…Furthermore, to show the synthetic application of this method, we have synthesized scaffold 2 t in 81% yield after 24 hrs (Scheme 2A). This intermediate ( 2 t ) is subsequently brominated according to the literature method to afford elastage inhibitor [11] . Moreover, a gram scale reaction was performed with 10 mmol of 1 a using the optimized reaction condition, affording 79% (1.8 g) of 2 a (Scheme 2B).…”

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

“…The research groups of Zeng and Chen established a novel metal-free oxidative-amidation protocol for the synthesis of αketothioamides (78) and amides (77) from α-azido ketones (76). [105] When elemental sulphur was used to thionate the CÀ H bond of α-azido ketones, it could create α-ketothioacyl azide, which amines could then attack nucleophilically to break the CÀ N bond and produce α-ketothioamides (Scheme 25). While in the presence of PIDA, selective CÀ C bond cleavage could result in the formation of amides along with the release of nitrogen gas and cyano anion.…”

“…The cyclometalated alkoxy-Pd(IV)-alkyl that resulted from oxidation then went through direct reductive elimination to produce a polycyclic oxa-heterocycle. Instead, an SN 2 -type CÀ C reductive elimination of alkyl-Pd(IV) took place together with hydroxy acetylation when another coordinating site or ligand accessible by palladium was present, producing 3-bicyclo[4.1.0]heptan-5one products (105).…”