Wang M,
Huang Y,
Hu P.
*
Sun Yat-Sen University, Guangzhou, P. R. of China
Terminal C(sp
3)–H Borylation through Intermolecular Radical Sampling.
Science 2024;
383: 537-544
DOI:
10.1126/science.adj9258
Key words
photocatalysis - HAT - iron catalysis - borylation
Significance
Wang and co-workers report a terminal sp3 C–H borylation under photocatalytic conditions. Products arising from 2° and 3° C–H group functionalization were found in low yields. The regioselectivity was attributed to radical sampling due to varying steric encumbrance between radicals.
Comment
Key to enabling the observed selectivity was the inclusion of a sulfoxide to enable reversible HAT from a borinic acid sulfoxide complex. Interestingly the use of the sulfide rather than sulfoxide led to no apparent selectivity between regioisomers.
