Switchable C-H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes

Area of Science:

• Organic Chemistry
• Catalysis
• Synthetic Methodology

Background:

• Directing group or catalyst-dependent C-H functionalization often leads to divergent reaction pathways.
• Developing switchable synthetic methods is crucial for efficient molecular construction.

Purpose of the Study:

• To report a controllable rhodium-catalyzed protocol for the alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane.
• To demonstrate the switchable nature of the reaction manifold based on the intrinsic properties of acryloyl silane.

Main Methods:

• Rhodium-catalyzed reaction.
• Utilizing N-tosyl acrylamide and acryloyl silane as substrates.
• Modification of reaction conditions to control product outcome.

Main Results:

• Achieved controllable alkylation and alkenylation-annulation.
• Demonstrated that acryloyl silane's intrinsic properties enable switchable reaction pathways.
• Obtained either alkylation or annulation products by slight modification of reaction conditions.

Conclusions:

• The developed rhodium-catalyzed protocol offers a versatile approach for synthesizing diverse molecular structures.
• The intrinsic reactivity of acryloyl silane provides a unique advantage for controlling reaction outcomes in C-H functionalization.