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. 2019 Jul 19;21(14):5689-5693.
doi: 10.1021/acs.orglett.9b02029. Epub 2019 Jul 2.

Rhodium(III)-Catalyzed C-H Activation: Ligand-Controlled Regioselective Synthesis of 4-Methyl-Substituted Dihydroisoquinolones

Joyann S Barber  1 , Stephanie Scales  1 , Michelle Tran-Dubé  1 , Fen Wang  1 , Neal W Sach  1 , Louise Bernier  1 , Michael R Collins  1 , JinJiang Zhu  1 , Indrawan J McAlpine  1 , Ryan L Patman  1
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Rhodium(III)-Catalyzed C-H Activation: Ligand-Controlled Regioselective Synthesis of 4-Methyl-Substituted Dihydroisoquinolones

Joyann S Barber et al. Org Lett. .

Abstract

Rh-catalyzed C-H functionalization of O-pivaloyl benzhydroxamic acids with propene gas provides access to 4-methyl-substituted dihydroisoquinolones. Good to excellent levels of regioselectivity are achieved using [CptRhCl2]2 as a precatalyst under optimized conditions. Thorough examination of aryl/heteroaryl O-pivaloyl hydroxamic acid substrates, ligand effects on C-H site selectivity, alkene scope, and demonstration of scale are discussed within.

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