Continuous Photoflow Synthesis of Heterohelicenes.

Area of Science:

• Organic chemistry
• Materials science

Background:

• Heterohelicenes are of significant interest for their applications as organic chiral materials.
• There is a growing demand for novel heterohelicene structures, necessitating efficient and scalable synthetic methods.

Purpose of the Study:

• To develop an expedient and scalable synthetic procedure for novel heterohelicene structures.
• To adapt the Mallory photocyclization methodology for continuous flow synthesis.

Main Methods:

• Utilized a Mallory photocyclization reaction.
• Implemented the synthesis in a continuous flow system.
• Applied the method to the synthesis of thia-, oxa-, and azahelicenes.

Main Results:

• Successfully synthesized thia-, oxa-, and azahelicenes using the continuous flow Mallory photocyclization.
• The procedure was scaled up to 9.8 mmol, demonstrating scalability.
• The methodology is suitable for iterative modular synthesis.

Conclusions:

• The continuous flow Mallory photocyclization offers an efficient and scalable route to diverse heterohelicenes.
• This method addresses the need for rapid access to novel organic chiral materials.
• The iterative modular nature of the synthesis allows for facile structural diversification.