Organic chemistry articles from across Nature Portfolio

Site-selective C–H bond functionalization of silanes is challenging because of the presence of multiple C–H bonds. Now, a photocatalytic method for the radical β-C(sp³)–H functionalization of silanes using the β-silicon effect is developed, enabling the aminoalkylation, alkylation and arylation of simple silanes to prepare more complex organosilicon compounds.

A glaring gap in the portfolio of reactions used to synthesize libraries of organic compounds has been filled by the advent of a general method for joining together 3D molecular fragments — a boon for pharmaceutical research.

Despite advances, a general olefination strategy for the direct conversion of carboxylic acids, alcohols and alkanes into alkenes remains challenging owing to their inherent differences in reactivity. Now, a one-pot photochemical method comprising a Giese addition followed by a Norrish type-II fragmentation enables the on-demand production of alkenes from diverse substrates.

The current throughput of conventional organic chemical synthesis is usually a few experiments for each operator per day. Here the authors develop a robotic system for ultra-high-throughput chemical synthesis, online characterization and large-scale condition screening of photocatalytic reactions.

Ozonolysis reactions convert alkenes into carbon–oxygen compounds via C=C bond cleavage. Now the cleavage of alkenes to form carbon–nitrogen bonds—the aza version of ozonolysis, termed triazenolysis—has been developed. The reaction produces diamines from cyclic alkenes, while acyclic C=C bonds are broken to generate two separate amine units.

Site-selective C–H functionalization of silanes is challenging because of the presence of multiple C–H bonds in the same molecule. Now a general photocatalytic site-selective radical functionalization of organosilicon compounds is reported, enabled by the β-silicon effect, which activates β-C(sp³)–H bonds. These reactions are applicable to linear and complex cyclic silanes.

Chiral tertiary alcohols are an important structural motif, but the general methodologies for the synthesis are less reported. Herein, the authors report a Ni(ІІ)-catalyzed asymmetric alkenylation and arylation of aryl ketones with organoborons under air via a 1,5-metalate shift to obtain chiral tertiary allylic alcohols and diaryl alcohols.

Machine learning has been used to reveal the relationship between protein sequences and biocatalytic enantioselectivity, but the establishment of substrate fitness space is challenging. Herein, the authors build random forest classification models for predicting the enantioselectivity of amidase toward different substrates, adopting chemistry and geometry descriptors.

Site-selective C–H bond functionalization of silanes is challenging because of the presence of multiple C–H bonds. Now, a photocatalytic method for the radical β-C(sp³)–H functionalization of silanes using the β-silicon effect is developed, enabling the aminoalkylation, alkylation and arylation of simple silanes to prepare more complex organosilicon compounds.

A glaring gap in the portfolio of reactions used to synthesize libraries of organic compounds has been filled by the advent of a general method for joining together 3D molecular fragments — a boon for pharmaceutical research.

Despite advances, a general olefination strategy for the direct conversion of carboxylic acids, alcohols and alkanes into alkenes remains challenging owing to their inherent differences in reactivity. Now, a one-pot photochemical method comprising a Giese addition followed by a Norrish type-II fragmentation enables the on-demand production of alkenes from diverse substrates.

2024 marks twenty years of the educational website Not Voodoo: Demystifying Synthetic Organic Chemistry — a fount of knowledge for organic chemistry laboratory techniques, with tips and tricks for both beginning research students and advanced experimentalists. 

The translocation of alkenes and remote functional groups is an ingenious strategy to reorganize complex structures, yet it is rarely investigated, owing to the challenges in controlling multiple selectivities. Now, an efficient photo/cobalt dual-catalytic method has been developed to accomplish alkene difunctionalization.