The advent of click chemistry has had a profound impact on many fields and fueled a need for reliable reactions to expand the click chemistry toolkit. However, developing new systems to fulfill the click chemistry criteria remains highly desirable yet challenging. Here, we report the development of light-induced primary amines and o-nitrobenzyl alcohols cyclization (PANAC) as a photoclick reaction via primary amines as direct click handle, to rapid and modular functionalization of diverse small molecules and native biomolecules. With intrinsic advantages of temporal control, good biocompatibility, reliable chemoselectivity, excellent efficiency, readily accessible reactants, operational simplicity and mild conditions, the PANAC photoclick is robust for direct diversification of pharmaceuticals and biorelevant molecules, lysine-specific modifications of unprotected peptides and native proteins in vitro, temporal profiling of endogenous kinases and organelle-targeted labeling in living systems. This strategy provides a versatile platform for organic synthesis, bioconjugation, medicinal chemistry, chemical biology and materials science.

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An efficient palladium‐catalyzed tandem addition/cyclization of 2′‐formyl‐[1,1′‐biaryl]‐2‐carbonitriles with arylboronic acids is reported. This reaction affords dibenzo[c,e]azepin‐5‐ols and benzo[c]pyrido[2,3‐e]azepin‐5‐ols with excellent selectivity and wide functional group compatibility. The dibenzo[c,e]azepin‐5‐ols show good cell growth inhibitory activity against a triple‐negative breast cancer cell line. Moreover, the proposed mechanistic rationale for this tandem process is supported by theoretical calculations.magnified image