ArticleThe Journal of organic chemistry2026
Stereoselective Prenylation of Aryl- and Heteroaryl Halides: γ-Selective Suzuki-Miyaura Coupling as a Tool for Asymmetric Csp
Article in The Journal of organic chemistry, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
The stereoselective preparation of all carbon quaternary stereogenic centers attached to an aromatic core structure is a long-standing challenge for synthetic chemists, due to the sterically encumbered nature of the central carbon atom. Natural products, like teleocidin A or sporochnol A, carrying a branched geranyl chain feature this special and challenging structural motif. Herein, we present a catalytic system that promotes the asymmetric γ-selective Suzuki-Miyaura cross-coupling of aryl halides and allyl boronic acid esters, to form the desired stereogenic center in one step. The γ-selective coupling approach overcomes the need for a preformed stereogenic center, gives selective access to both stereoisomers, and starts with readily available starting materials. In this study we investigate the scope of the γ-selective cross-coupling reaction and showcase its applicability for late-stage derivatization and natural product synthesis, to provide a further asset in the toolbox of asymmetric synthesis.
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