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Rhodium catalyzed synthesis of isoindolinones via C-H activation of N-benzoylsulfonamides.

ABSTRACT: An efficient approach to a wide range of isoindolinones, including 3-monosubstituted and 3,3-disubstituted isoindolinones, from the annulation of N-benzoylsulfonamides with olefins and diazoacetate has been developed. The transformation is broadly compatible with both terminal and internal olefins. Moreover, diazoacetate is for the first time incorporated into an amide-directed C-H functionalization reaction. Specifically, the rhodium complex [{RhCl(2)Cp*}(2)] enables the in situ dimerization of diazoacetate in addition to its role in catalyzing C-H functionalization/cross-coupling.

SUBMITTER: Zhu C

PROVIDER: S-EPMC3472453 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature

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Rhodium catalyzed synthesis of isoindolinones via C-H activation of N-benzoylsulfonamides.

Zhu Chen C Falck John R JR

Tetrahedron 20120904 45

An efficient approach to a wide range of isoindolinones, including 3-monosubstituted and 3,3-disubstituted isoindolinones, from the annulation of N-benzoylsulfonamides with olefins and diazoacetate has been developed. The transformation is broadly compatible with both terminal and internal olefins. Moreover, diazoacetate is for the first time incorporated into an amide-directed C-H functionalization reaction. Specifically, the rhodium complex [{RhCl(2)Cp*}(2)] enables the in situ dimerization of ...[more]

PMID: 23087489

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