Shu, Chao published the artcileMetal-free photoinduced C(sp3)-H borylation of alkanes, Recommanded Product: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, the publication is Nature (London, United Kingdom) (2020), 586(7831), 714-719, database is CAplus and MEDLINE.
Boronic acids and their derivatives are some of the most useful reagents in the chem. sciences, with applications spanning pharmaceuticals, agrochems. and functional materials. Catalytic C-H borylation is a powerful method for introducing these and other boron groups into organic mols. because it can be used to directly functionalize C-H bonds of feedstock chems. without the need for substrate pre-activation. These reactions have traditionally relied on precious-metal catalysts for C-H bond cleavage and, as a result, display high selectivity for borylation of aromatic C(sp2)-H bonds over aliphatic C(sp3)-H bonds. Here we report a mechanistically distinct, metal-free borylation using hydrogen atom transfer catalysis, in which homolytic cleavage of C(sp3)-H bonds produces alkyl radicals that are borylated by direct reaction with a diboron reagent. The reaction proceeds by violet-light photoinduced electron transfer between an N-alkoxyphthalimide-based oxidant and a chloride hydrogen atom transfer catalyst. Unusually, stronger Me C-H bonds are borylated preferentially over weaker secondary, tertiary and even benzylic C-H bonds. Mechanistic studies indicate that the high Me selectivity is a result of the formation of a chlorine radical-boron ‘ate’ complex that selectively cleaves sterically unhindered C-H bonds. By using a photoinduced hydrogen atom transfer strategy, this metal-free C(sp3)-H borylation enables unreactive alkanes to be transformed into valuable organoboron reagents under mild conditions and with selectivities that contrast with those of established metal-catalyzed protocols.
Nature (London, United Kingdom) published new progress about 238088-16-9. 238088-16-9 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Aliphatic cyclic hydrocarbon,Boronic Acids,Boronate Esters, name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, and the molecular formula is C3H9ClOS, Recommanded Product: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile.
Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts