Ligand-controlled regiodivergent arylation of aryl(alkyl)alkynes and asymmetric synthesis of axially chiral 9-alkylidene-9,10-dihydroanthracenes

Chao Sun, Ting Qi, Faiz-Ur Rahman, Tamio Hayashi () and Jialin Ming ()
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Chao Sun: Inner Mongolia University
Ting Qi: Chengdu University
Faiz-Ur Rahman: Inner Mongolia University
Tamio Hayashi: National Taiwan Normal University
Jialin Ming: Inner Mongolia University

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: Abstract Transition metal-catalyzed addition of organometallics to aryl(alkyl)alkynes has been well known to proceed with the regioselectivity in forming a carbon–carbon bond at the alkyl-substituted carbon (β-addition). Herein, the reverse regiochemistry with high selectivity in giving 1,1-diarylalkenes (α-addition) was realized in the reaction of arylboronic acids with aryl(alkyl)alkynes by use of a rhodium catalyst coordinated with a chiral diene ligand, whereas the arylation of the same alkynes proceeded with the usual regioselectivity (β-addition) in the presence of a rhodium/DM-BINAP catalyst. The regioselectivity can be switched by the choice of ligands on the rhodium catalysts. This reverse regioselectivity also enabled the catalytic asymmetric synthesis of phoenix-like axially chiral alkylidene dihydroanthracenes with high enantioselectivity through an α-addition/1,4-migration/cyclization sequence.

Date: 2024
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DOI: 10.1038/s41467-024-53767-4

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