title: Oxidative coupling of NH isoquinolones with olefins catalyzed by Rh(III).
abstract: Rh(III)-catalyzed oxidative coupling reactions between isoquinolones with 3-aryl groups and activated olefins have been achieved using anhydrous Cu(OAc)(2) as an oxidant to give tetracyclic products. The nitrogen atom acts as a directing group to facilitate ortho C-H activation. This reaction can be one-pot starting from methyl benzohydroxamates, without the necessity of the isolation of isoquinolone products. A broad scope of substrates has been demonstrated, and both terminal and internal activated olefins can be applied. In the coupling of N-methylmaleimide, a Wacker-like mechanism was proposed, where backside attack of the NH group in isoquinolones is suggested as a key step. Selective C-H activation has also been achieved at the 8-position of 1-naphthol, leading to an olefination product.
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.
authors.forename: Fen
authors.initials: F
authors.lastname: Wang
authors.forename: Guoyong
authors.initials: G
authors.lastname: Song
authors.forename: Zhengyin
authors.initials: Z
authors.lastname: Du
authors.forename: Xingwei
authors.initials: X
authors.lastname: Li