Bio-inspired Halogen Bonding-Promoted Cross Coupling for the Synthesis of Organoselenium Compounds

Noncovalent interactions play fundamental roles in many organic and biochemical processes, including hydrogen and halogen bonding, which are vital in the fields of synthesis and catalysis. Herein, we describe the application of halogen bonding interactions to facilitate the reaction balance between an electron donor-acceptor (EDA) complex and Ph2Se2 for the synthesis of a series of organoselenium compounds. The EDA complex concept has recently emerged as an attractive path for visible light-induced transformations due to facile reaction conditions and the avoidance of photocatalysts. Density functional theory calculations reveal that an iodine-pi* interaction leads to the formation of an alkyl radical from the N-(acyloxy)phthalimide ester. The resulting alkyl radical is captured by the diselenide-I center dot complex to form the C-Se bond. The developed selenide synthesis strategy has been applied in the transformation of primary, secondary, and tertiary carboxylic acids as well as a series of natural products, drugs, and alpha-selenoamino acids.

Automated summary

Noncovalent interactions, particularly halogen bonding, play a crucial role in organic synthesis and catalysis, including the synthesis of organoselenium compounds. By utilizing the reaction balance between an electron donor-acceptor complex and Ph2Se2, the halogen bonding interaction facilitates the formation of C-Se bonds through the capture of alkyl radicals. This synthetic strategy has been successfully applied in the transformation of various carboxylic acids, natural products, drugs, and alpha-selenoamino acids.