Experimental study demonstrates a protecting-group-free synthesis of cannabidiol analogs using perfluoroboronic acid, highlighting a practical platform for late-stage cannabinoid functionalization.
A concise, protecting‐group‐free approach to a cannabidiol (CBD)‐type scaffold is described via the Friedel–Crafts allylation of phloroglucinol with (–) ‐p ‐mentha‐2,8‐dien‐1‐ol. Utilizing pentafluorophenylboronic acid [C 6 F 5 B(OH) 2 ] as a mild Lewis acid in an HFIP/THF solvent system efficiently suppresses competing THC‐type cyclization, delivering the desired non‐cyclized CBD intermediate ( 3a ) in >60% yield. While C‐2 versus C‐4 regioselectivity is governed by the steric and electronic properties of the resorcinol substrates [e.g., 3b (9%) vs. 4b (53%), and 3c (43%) vs. 4c (8%)], the transformation efficiency can be maximized via regioselective triflation of 3a . Subsequent palladium‐mediated cross‐couplings of the resulting triflate yielded diverse CBD analogs, establishing a practical platform for the late‐stage modification of functionalized cannabinoid‐like molecules.
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Khatri et al. (2026) studied this question.
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