Indazolones Directed Rh(III)‐Catalyzed C−H Amidation of Arenes

Abstract

The Cp*Rh(III)-catalyzed indazolone-directed CÀ H bond amidation of arenes has been realized by employing sulfonyl azide agents and dioxazolones as nitrogen source. This protocol displays mild conditions, broad substrate scope and high functional group compatibility. What' more, the late-stage modifications of structure complicated drugs, such as Gemfibrozil, Oxaprozin, Probenecid and Naproxen, has been demonstrated. Furthermore, preliminary mechanistic investigation and an exploratory reaction mechanism were also proposed.

Rh(III)-Catalyzed C–H Functionalization/Annulation of 1-Arylindazolones: Divergent Synthesis of Fused Indazolones and Allyl Indazolones

“…Over the past decade, Rh­(III)-catalyzed inert C–H functionalization/annulation reactions have been extensively explored by Glorius, Li, and other groups . Driven by our ongoing interest in the Rh­(III) catalytic C–H functionalization and cyclization reaction, and our previous work on the diversified synthetic transformation of 2-methylidenetrimethylene carbonate, we herein describe the Rh­(III)-catalyzed C–H/N–H annulation and C–H allylation of phenylindazolones for the first time (Scheme b). This novel protocol was conducted mainly by employing 5-methylene-1,3-dioxan-2-one and 4-vinyl-1,3-dioxolan-2-one as scalable cross-coupling partners, delivering the corresponding cyclization products and allylated products (total 33 examples) in moderate to excellent yield.…”