Asymmetric Cross-Coupling via Photoredox Catalysis

The proposed project is to develop a method to cross-couple organic feedstock molecules using base metals and photocatalysts. The method will utilize photocatalysts to convert inert C-H bonds into highly reactive radicals that can be captured using a base metal catalyst. The hydrogen atom is an ideal coupling handle, considering its abundance in organic molecules and its availability for functionalization at almost any stage in a synthetic sequence. This strategy would that avoid the need for substrate prefunctionalization, selectively converting C(sp3)–H bonds directly into C–C bonds. The ability to directly couple these aliphatic C-H bonds with two of the most abundant alkyl sources (carboxylic acids and amines) would grant rapid access to sp3-rich products in a single-step, facilitating a practical synthesis of aliphatic motifs that would be exceedingly difficult to access with traditional methods.

Faculty Supervisor:

Mark Lautens

Student:

Partner:

University of Bologna

Discipline:

Physics

Sector:

Pharmaceuticals; Life Sciences (not health); Agriculture and Food

University:

University of Toronto

Program: