Co(III)-Catalyzed, N-Amino-Directed C-H Coupling with 4-Hydroxy-2-Alkynoates for Indole Synthesis

Conventional synthetic organic chemistry typically relies on site-centered reactivity for reaction discovery. Herein, skeleton-chaperoned reactivity is exploited for reaction development, with skeleton utilized as a structural scaffold for assisting functional group activation into a proper reactivity sequence. A Co(III) catalytic method has been developed for N-amino-directed C-H coupling with 4-hydroxy-2-alkynoates, allowing convenient access to 2-alkene-3-carboxylic acid type indole derivatives. This reaction features phenyl/pyrrole/lactone skeleton-chaperoned reactivity and simultaneous conversions of five functional groups. Given the vast pool of skeletons available for structural scaffolding, skeleton-chaperoned reactivity promises to become a powerful tool for divergent entry into distinct chemical space.