The catalytic functionalization of unreactive C-H bonds is an area of growing importance for the design of atom economical strategies to valuable organic molecules. However, due to the ubiquity of C-H bonds in organic molecules, achieving perfect site-selectivity and high functional group tolerance has been one of the major challenges in this area. In this context, this dissertation outlines our efforts to develop key structure building C-H functionalization reactions that streamline the construction of complex molecular skeletons based on the use of 2-pyridyl-containing directing groups.
In particular, we have achieved:
- The construction of C-N bonds through a Cu-catalyzed cross-dehydrogenative coupling strategy.
- The development of a Rh-catalyzed tandem process that involves the formation of C-C and C-X bonds.
- A switchable site-selectivity through catalyst control in the direct Rh-catalyzed functionalization of molecule that contain distinct C-H bonds.
- A catalyst-controlled selectivity in the Rh-catalyzed C(sp2)–H functionalization with 1,3-diynes involving cyclization cascade processes.
- The Co-catalyzed alkyne annulation of N-containing arenes through C-H/N-H functionalization.
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