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Synfacts 2024; 20(04): 0369
DOI: 10.1055/s-0043-1773145
Metals in Synthesis

Terminal C–H Borylation Enabled by Visible Light Iron Photocatalysis

Contributor(s):
Mark Lautens
,
Colton E. Johnson
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
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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.


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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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