Ligand design for Rh(iii)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones† †Electronic supplementary information (ESI) available: Experimental procedures and compound characterization. CCDC 1021286. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4sc02590c Click here for additional data file. Click here for additional data file.
نویسندگان
چکیده
We report the regioselective synthesis of dihydroisoquinolones from aliphatic alkenes and O-pivaloyl benzhydroxamic acids mediated by a Rh(III) precatalyst bearing sterically bulky substituents. While the prototypical Cp* ligand provides product with low selectivity, sterically bulky Cpt affords product with excellent regioselectivity for a range of benzhydroxamic acids and alkenes. Crystallographic evidence offers insight as to the source of the increased regioselectivity.
منابع مشابه
Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis† †Electronic supplementary information (ESI) available. CCDC 1499990. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc03888c Click here for additional data file. Click here for additional data file.
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Heptamethylindenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(iii)-catalyzed C–H activation† †Electronic supplementary information (ESI) available: Experimental procedures and compound characterization. CCDC 1472771. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc02587k Click here for additional data file. Click here for additional data file. Click here for additional data file.
The diastereoselective coupling of O-substituted arylhydroxamates and cyclopropenes mediated by Rh(III) catalysis was successfully developed. Through ligand development, the diastereoselectivity of this reaction was improved using a heptamethylindenyl (Ind*) ligand, which has been rationalized using quantum chemical calculations. In addition, the nature of the O-substituted ester of benzhydroxa...
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Taddol-based phosphoramidite ligands enable enantioselective palladium(0)-catalyzed C–H arylation of cyclopropanes. The cyclized products are obtained in high yields and enantioselectivities. The reported method provides efficient access to a broad range of synthetically attractive cyclopropyl containing dihydroquinolones and dihydroisoquinolones as well as allows for an efficient enantioselect...
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