igand-Accelerated ortho-C-H Olefination of Phenylacetic Acids

Methods for functionalizing carbon–hydrogen bonds are featured in a new synthesis of the tricyclic core architecture that characterizes the indoxamycin family of secondary metabolites. A unique collaboration between three laboratories has engendered a design for synthesis featuring two sequential C−H functionalization reactions, namely a diastereoselective dirhodium carbene insertion followed by an ester‐directed oxidative Heck cyclization, to rapidly assemble the congested tricyclic core of the indoxamycins. This project exemplifies how multi‐laboratory collaborations can foster conceptually novel approaches to challenging problems in chemical synthesis.

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Rapid Construction of a Benzo‐Fused Indoxamycin Core Enabled by Site‐Selective C−H Functionalizations

Bedell

Hone

Valette

et al. 2016

Angewandte Chemie

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Rapid Construction of a Benzo‐Fused Indoxamycin Core Enabled by Site‐Selective C−H Functionalizations

et al. 2016

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Methods for functionalizing carbon-hydrogen bonds are featured in a new synthesis of the tricyclic core architecture that characterizes the indoxamycin family of secondary metabolites. A unique collaboration between three laboratories has engendered a design for synthesis featuring two sequential C-H functionalization reactions, namely a diastereoselective dirhodium carbene insertion followed by an ester-directed oxidative Heck cyclization, to rapidly assemble the congested tricyclic core of the indoxamycins. This project exemplifies how multi-laboratory collaborations can foster conceptually novel approaches to challenging problems in chemical synthesis.

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Transition-Metal-Catalyzed Direct Addition of Aryl C-H Bonds to Unsaturated Electrophiles

Shi¹,

Han²,

Li³

2016

The Chemical Record

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The direct addition of Csp(2) -H bonds onto polar C=C, C=O, and C=N bonds is both synthetically and mechanistically important, because using aromatic C-H substrates in place of organometallic reagents provides a more direct and atom-economical alternative to many important compounds without the pre-generation of organometallic compounds from stoichiometric halides and the unavoidable generation of stoichiometric metal halide waste. In this account, we summarize our contributions to the transition-metal-catalyzed addition of aromatic C-H bonds to polar C=C, C=O, and C=N bonds via directing-group-assisted regiospecific reactions. These synthetic methods provide efficient access to benzylic alcohols, alkylbenzenes, 3-substituted phthalides, N-substituted phthalimides, N-aryl benzamides, and indene derivatives from commercially available reagents. It is worth noting that valuable heterocycles such as 3-substituted phthalides and N-substituted phthalimides can be obtained in one step by this approach.

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igand-Accelerated ortho-C-H Olefination of Phenylacetic Acids

Abstract: Graphical abstract

Cited by 4 publications

References 81 publications

Rapid Construction of a Benzo‐Fused Indoxamycin Core Enabled by Site‐Selective C−H Functionalizations

Rapid Construction of a Benzo‐Fused Indoxamycin Core Enabled by Site‐Selective C−H Functionalizations

Rapid Construction of a Benzo‐Fused Indoxamycin Core Enabled by Site‐Selective C−H Functionalizations

Transition-Metal-Catalyzed Direct Addition of Aryl C-H Bonds to Unsaturated Electrophiles

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