Zhu, Feng published the artcileCatalytic and Photochemical Strategies to Stabilized Radicals Based on Anomeric Nucleophiles, Safety of 1-(Chloromethyl)-4-(trifluoromethyl)benzene, the publication is Journal of the American Chemical Society (2020), 142(25), 11102-11113, database is CAplus and MEDLINE.
Carbohydrates, one of the three primary macromols. of living organisms, play significant roles in various biol. processes such as intercellular communication, cell recognition, and immune activity. While the majority of established methods for the installation of carbohydrates through the anomeric carbon rely on nucleophilic displacement, anomeric radicals represent an attractive alternative because of their functional group compatibility and high anomeric selectivities. Herein, we demonstrate that anomeric nucleophiles such as C1 stannanes can be converted into anomeric radicals by merging Cu(I)-catalysis with blue light irradiation to achieve highly stereoselective C(sp3)-S cross-coupling reactions. Mechanistic studies and DFT calculations revealed that the C-S bond-forming step occurs via the transfer of the anomeric radical directly to a sulfur electrophile bound to Cu(II) species. This pathway complements a radical chain observed for metal-free conditions where a disulfide initiator can be activated by a Lewis base additive. Both strategies utilize anomeric nucleophiles as efficient radical donors and achieve a switch from an ionic to a radical pathway. Taken together, the stability of glycosyl nucleophiles, a broad substrate scope, and high anomeric selectivities observed for the thermal and photochem. protocols make this novel C-S cross-coupling a practical tool for late-stage glyco-diversification of bioactive natural products and drug candidates.
Journal of the American Chemical Society published new progress about 939-99-1. 939-99-1 belongs to chlorides-buliding-blocks, auxiliary class Fluoride,Chloride,Benzyl chloride,Benzene, name is 1-(Chloromethyl)-4-(trifluoromethyl)benzene, and the molecular formula is C4H5BN2O2, Safety of 1-(Chloromethyl)-4-(trifluoromethyl)benzene.
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