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Synfacts 2024; 20(04): 0369
DOI: 10.1055/s-0043-1773145
DOI: 10.1055/s-0043-1773145
Metals in Synthesis
Terminal C–H Borylation Enabled by Visible Light Iron Photocatalysis
Wang M,
Huang Y,
Hu P.
*
Sun Yat-Sen University, Guangzhou, P. R. of China
Terminal C(sp3)–H Borylation through Intermolecular Radical Sampling.
Science 2024;
383: 537-544
DOI: 10.1126/science.adj9258
Terminal C(sp3)–H Borylation through Intermolecular Radical Sampling.
Science 2024;
383: 537-544
DOI: 10.1126/science.adj9258
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.
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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.
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Publication History
Article published online:
13 March 2024
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