Project Summary – Iodine Catalyzed Cross-Coupling Reactions
The proposed research aims to discover and develop economical, environmentally- and user-friendly iodine
catalyzed cross-coupling reactions for the synthesis of key chemical bonds (carbon-nitrogen and carbon-
carbon bonds), functional groups (amides, imides and ketones) and frameworks (nitrogen-containing
heterocycles such as pyrrole). Despite the great interest and efforts devoted in cross-coupling reactions,
examples of iodine catalyzed cross-coupling still remain scarce compared to the number of protocols mediated
by transition metal catalysts. The proposal is grounded in our preliminary results that acyl radical species are
readily generated from aldehyde substrates in the presence of an iodine/potassium persulfate catalyst system,
which participate in coupling reactions with a variety of chemical compounds containing nitrogen nucleophiles.
Upon the completion of the proposed work, three specific aims will be accomplished: 1) a facile iodine
catalyzed carbon-nitrogen bond formation protocol for the preparation of amides and imides will be developed;
2) an iodine catalyzed carbon-carbon bond formation reaction via radical addition mechanism will be
developed; 3) a carbon-carbon bond formation reaction via an iodine and first-row late transition metal co-
catalyzed cross-coupling mechanism will be developed. The new methods are expected to serve the critical
needs of synthetic and medicinal chemists in preparation of the corresponding chemical bonds and
frameworks for novel therapeutics. A thorough investigation of the proposed iodine catalysis mechanism will be
conducted, which is expected to yield a comprehensive understanding of the proposed iodine catalysis and
serve as a template for future study in the field. In addition, the proposal will improve and strengthen the
infrastructure of research and education at Queens College. It will not only provide research opportunities to
the many underrepresented minority students among the Queens College undergraduates, but also will help
nurture the young generation of scientists who are interested in pursuing a research career in the STEM
disciplines.
Public Health Relevance Statement
Project Narrative – Iodine Catalyzed Cross-Coupling Reactions
The proposal aims at developing the mechanism for green synthetic protocols of a few key chemical bonds,
functional groups, and frameworks prevalently appearing in modern drug molecules. It focuses on the study of
coupling reactions for carbon-carbon and carbon-nitrogen bond formations. The proposed iodine-catalyzed
cross-couplings have obvious advantages over the transition metal-catalyzed coupling protocols widely
employed in the drug molecule synthesis for using an inexpensive green catalyst and effectively avoiding toxic
metal catalyst residues in final drug molecules. The new methods are expected to serve the critical need for
medicinal chemists in the course of preparing the corresponding chemical bonds and frameworks for novel
therapeutics.
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