Remote-carbonyl-directed sequential Heck/isomerization/C(sp2)–H arylation of alkenes for modular synthesis of stereodefined tetrasubstituted olefins

Runze Luan, Ping Lin, Kun Li, Yu Du () and Weiping Su ()
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Runze Luan: Chinese Academy of Sciences
Ping Lin: Chinese Academy of Sciences
Kun Li: Chinese Academy of Sciences
Yu Du: Chinese Academy of Sciences
Weiping Su: Chinese Academy of Sciences

Nature Communications, 2024, vol. 15, issue 1, 1-10

Abstract: Abstract Modular and regio-/stereoselective syntheses of all-carbon tetrasubstituted olefins from simple alkene materials remain a challenging project. Here, we demonstrate that a remote-carbonyl-directed palladium-catalyzed Heck/isomerization/C(sp2)–H arylation sequence enables unactivated 1,1-disubstituted alkenes to undergo stereoselective terminal diarylation with aryl iodides, thus offering a concise approach to construct stereodefined tetrasubstituted olefins in generally good yields under mild conditions; diverse carbonyl groups are allowed to act as directing groups, and various aryl groups can be introduced at the desired position simply by changing aryl iodides. The stereocontrol of the protocol stems from the compatibility between the E/Z isomerization and the alkenyl C(sp2)–H arylation, where the vicinal group-directed C(sp2)–H arylation of the Z-type intermediate product thermodynamically drives the reversible E to Z isomerization. Besides, the carbonyl group not only promotes the Pd-catalyzed sequential transformations of unactivated alkenes by weak coordination, but also avoids byproducts caused by other possible β-H elimination.

Date: 2024
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DOI: 10.1038/s41467-024-46051-y

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