Rhodium(III)-Catalyzed C–H Functionalization in Water for Isoindolin-1-one Synthesis

Rhodium-catalyzed green synthesis of isoindolin-1-ones via a sequential C–H activation/allene formation/cyclization pathway by applying water as solvent is reported. The reaction is highly regioselective, tolerating some potentially useful functional groups

Room-Temperature Synthesis of Trisubstituted Allenylsilanes via Regioselective C–H Functionalization

A Rh­(III)-catalyzed <i>o</i>-C–H bond functionalization-based allenyl­ation reaction of allenyl­silanes <b>2</b> with <i>N</i>-methoxy­benz­amides <b>1</b> affords poly-substituted allenyl­silanes with a wide range of attractive functional groups in moderate to excellent yields under very mild conditions (20 °C, compatible with ambient air and moisture). Those products may be transformed to different products with attractive structural features. Careful mechanistic studies suggest the reaction proceeds via <i>o</i>-rhodation, regioselective insertion, and β-H elimination

Room-Temperature Synthesis of Trisubstituted Allenylsilanes via Regioselective C–H Functionalization

A Rh­(III)-catalyzed <i>o</i>-C–H bond functionalization-based allenyl­ation reaction of allenyl­silanes <b>2</b> with <i>N</i>-methoxy­benz­amides <b>1</b> affords poly-substituted allenyl­silanes with a wide range of attractive functional groups in moderate to excellent yields under very mild conditions (20 °C, compatible with ambient air and moisture). Those products may be transformed to different products with attractive structural features. Careful mechanistic studies suggest the reaction proceeds via <i>o</i>-rhodation, regioselective insertion, and β-H elimination

A Straightforward Synthesis of Cyclobutenones via a Tandem Michael Addition/Cyclization Reaction of 2,3-Allenoates with Organozincs

An efficient method for synthesis of polysubstituted cyclobutenones, which are not readily available from traditional methods due to the intrinsic ring strain, is described. The reaction of 2,3-allenoates and organozinc reagents proceeds via a tandem Michael addition/cyclic 1,2-addition/elimination mechanism with the functional groups from the organozinc reagents being introduced to the 3-position of the cyclobutenone products regiospecifically in moderate to excellent yields. Application to the synthesis of stereodefined β,γ-unsaturated enones is demonstrated

A Straightforward Synthesis of Cyclobutenones via a Tandem Michael Addition/Cyclization Reaction of 2,3-Allenoates with Organozincs

An efficient method for synthesis of polysubstituted cyclobutenones, which are not readily available from traditional methods due to the intrinsic ring strain, is described. The reaction of 2,3-allenoates and organozinc reagents proceeds via a tandem Michael addition/cyclic 1,2-addition/elimination mechanism with the functional groups from the organozinc reagents being introduced to the 3-position of the cyclobutenone products regiospecifically in moderate to excellent yields. Application to the synthesis of stereodefined β,γ-unsaturated enones is demonstrated

A Straightforward Synthesis of Cyclobutenones via a Tandem Michael Addition/Cyclization Reaction of 2,3-Allenoates with Organozincs

An efficient method for synthesis of polysubstituted cyclobutenones, which are not readily available from traditional methods due to the intrinsic ring strain, is described. The reaction of 2,3-allenoates and organozinc reagents proceeds via a tandem Michael addition/cyclic 1,2-addition/elimination mechanism with the functional groups from the organozinc reagents being introduced to the 3-position of the cyclobutenone products regiospecifically in moderate to excellent yields. Application to the synthesis of stereodefined β,γ-unsaturated enones is demonstrated