Palladium-catalyzed asymmetric carbene coupling en route to inherently chiral heptagon-containing polyarenes

Huan Zhang, Chuan-Jun Lu, Gao-Hui Cai, Long-Long Xi, Jia Feng and Ren-Rong Liu ()
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Huan Zhang: Qingdao University
Chuan-Jun Lu: Qingdao University
Gao-Hui Cai: Qingdao University
Long-Long Xi: Qingdao University
Jia Feng: Qingdao University
Ren-Rong Liu: Qingdao University

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: Abstract Developing facile and direct synthesis routes for enantioselective construction of cyclic π-conjugated molecules is crucial. However, originate chirality from the distorted structure around heptagon-containing polyarenes is largely overlooked, the enantioselective construction of all-carbon heptagon-containing polyarenes remains a challenge. Herein, we present a highly enantioselective synthesis route for fabricating all carbon heptagon-containing polyarenes via palladium-catalyzed carbene-based cross–coupling of benzyl bromides and N-arylsulfonylhydrazones. A wide range of nonplanar, saddle-shaped tribenzocycloheptene derivatives are efficiently prepared in high yields with excellent enantioselectivities using this approach. In addition, stereochemical stability experiments show that these saddle-shaped tribenzocycloheptene derivatives have high inversion barriers.

Date: 2024
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DOI: 10.1038/s41467-024-47731-5

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