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Rhodium-Catalyzed C−H Functionalization and Seven-membered Ring Formation

Reporter: Dai Lu Supervisor: Prof. Zhao Jing Dr. Hong Mei

2013-12-23

Different Annulation Options for o-Vinylphenols

three different C−H positions

2-hydroxystyrene

chromene-type molecules

benzofuranes

Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2011, 76, 9548−9551.

oxepines

A Formal (5 + 2) Cycloaddition Reaction

Scope with Respect to the Alkyne Component

Phenols Equipped with Different Substituents

Proposed Mechanistic Cycle

(4 + 3) Annulations

benzamide furan-2-carboxamide

spiro dihydroisoquinolinone furan-fused azepinone

Proposed mechanism

(4 + 3) Annulations

vinylcarbenoids

(4 + 3) Annulations Angew. Chem. Int. Ed. 2013, 52, 5393 –5397

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