Rhodium-catalyzed reaction of diazoquinones with allylboronates to synthesize allylphenols?
Organic Chemistry Frontiers Pub Date: 2022-05-24 DOI: 10.1039/D2QO00626J
Abstract
Allylphenol is an important and ubiquitous structural motif in biologically active natural products and pharmaceuticals. Herein, we report a Rh2(esp)2-catalyzed reaction of diazoquinones with allylboronates, which provides access to a range of allylphenols, including para-allylphenols, ortho-allylphenols and allylnaphthols, in 44–94% yields and under mild conditions. The synthetic utility of the method was demonstrated by the short synthesis of two bioactive molecules. The mechanistic studies suggest that the reaction proceeds through a cyclopropanation/ring opening/aromatization pathway.
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Journal Name：Organic Chemistry Frontiers
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CAS no.: 89640-58-4
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