Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site-selective metabolic degradation of drugs and access radiotracers for positron emission tomography imaging. Despite current sophistication in fluorination reagents and processes, the fluorination of unactivated CH bonds remains a significant challenge. Reported herein is a convenient and economic process for direct fluorination of unactivated CH bonds that exploits the hydrogen abstracting ability of a decatungstate photocatalyst in combination with the mild fluorine atom transfer reagent N-fluorobenzenesulfonimide. This operationally straightforward reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acid derivatives.

A room-temperature, copper-catalyzed amination of primary benzylic C-H bonds with primary and secondary sulfonamides is described. The reaction is applicable to the coupling of a range of primary and secondary benzylic hydrocarbons with a diverse set of sulfonamides and is tolerant of substitution on both coupling partners. Factors which influence the selectivity of C-H functionalization between primary and secondary sites are examined.

Fluorination reactions are essential to modern medicinal chemistry, thus providing a means to block site‐selective metabolic degradation of drugs and access radiotracers for positron emission tomography imaging. Despite current sophistication in fluorination reagents and processes, the fluorination of unactivated CH bonds remains a significant challenge. Reported herein is a convenient and economic process for direct fluorination of unactivated CH bonds that exploits the hydrogen abstracting ability of a decatungstate photocatalyst in combination with the mild fluorine atom transfer reagent N‐fluorobenzenesulfonimide. This operationally straightforward reaction provides direct access to a wide range of fluorinated organic molecules, including structurally complex natural products, acyl fluorides, and fluorinated amino acid derivatives.

A total synthesis of the marine macrolide biselide A is described that relies on an enantiomerically enriched α-chloroaldehyde as the sole chiral building block.

A Convenient Photocatalytic Fluorination of Unactivated C-H Bonds. -A straightforward method for fluorination of unactivated C-H bonds is described. Alkyl fluorides of natural products and amino acids are obtained in moderate yields. Furthermore, aldehydes react to amides in the presence of amines. -(HALPERIN, S. D.; FAN, H.; CHANG, S.; MARTIN, R. E.; BRITTON*, R.; Angew. Chem., Int. Ed. 53 (2014) 18, 4690-4693, http://dx.

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The amination of secondary benzylic C—H bonds is also possible.

The general strategy for the synthesis of chromenopyridinones and pyridopyranoindazolones encompasses a directed ortho metalation (DoM)‐Suzuki‐Miyaura cross coupling and directed remote metalation (DreM) sequence.