Palladium-catalyzed asymmetric carbene coupling en route to inherently chiral heptagon-containing polyarenes.
Nat Commun
; 15(1): 3353, 2024 Apr 18.
Article
em En
| MEDLINE
| ID: mdl-38637535
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.
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MEDLINE
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En
Ano de publicação:
2024
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Article