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Biocatalytic strategies typically transform only one alkene isomer into products, limiting the yield. Now a biocatalyst is reported to convert both isomeric silyl enol ethers into chiral α-branched ketones with high efficiency and excellent selectivity.

Whileortho-selective C-H activation is well explored, general meta-selective methods are rare and often require directing groups that are retained in the final products. Here the authors show that transient imine groups can be used to direct the meta-functionalization of a range of arenes.

Chalcogen-containing compounds find broad application in chemical industry. Here, the authors report a nickel-catalyzed reductive chalcogenation of unactivated alkyl bromides with thiosulfonates and selenosulfonates to access a range of unsymmetrical sulfides and selenides under mild conditions.

Unlike the more common C–H functionalization, methods for the functionalization of C–C bonds are scarce. Here, Ackermann and co-workers show that an inexpensive manganese catalyst is capable of selectively activating C–C bonds for alkylations, alkenylations, and allylations in water.

Palladium-catalyzed late-stage diversification of structurally complex peptides has major shortcomings. Here, the authors developed a ruthenium-catalyzed C–H alkylations of peptides allowing for fluorescence labeling, late-stage diversifications and peptide ligations by solid phase peptide synthesis.

Direct stereoselective amination of tertiary C–H bonds without the assistance of directing groups is a challenging task in synthetic organic chemistry. Now a nitrene transferase is engineered to aminate tertiary C–H bonds with high enantioselectivity, providing direct access to valuable chiral α-tertiary primary amines.

Effective strategies for direct arene C−H functionalization are sought after. Here arene C−H functionalization via iridium nitrenoid-catalysed nucleophilic aromatic substitution allows the coupling of aryl azides with different carbon nucleophiles and is applied to the enantioselective synthesis of NOBINs

The design of efficient and selective catalysts is a formidable challenge in chemical science. Here the authors design a data-driven workflow to achieve the digitalized knowledge transfer between the synthetically relevant transformations, which was demonstrated in the prediction of chiral carboxylic acid co-catalyst for the cobalt-catalyzed asymmetric C–H alkylation of indoles.

This Primer provides an overview of the best practices for C–H activation as well as key advances in asymmetric, photoinduced and electrocatalytic-mediated catalysis for this synthetic platform. An overview of how C–H activation facilitates the synthesis of molecules such as structurally complex (bio)polymers and drugs is provided along with the current challenges and priorities for the next decade.