Nickel/Copper Co‐catalyzed Enantioselective Reductive Coupling of Oxabenzonorbornadienes with Vinyl Bromides

Deng, Yao; Meng, Yunyan; Yang, Qiongtong; Liu, Zixiu; Fan, Ruifeng; Chen, Jingchao; Fan, Baomin

doi:10.1002/adsc.202300633

Cited by 2 publications

(2 citation statements)

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“…The first advantage of L1 over L2 lies in its convenient synthesis from readily available precursors, making it attractive for large-scale syntheses. Pd complexes of L1 have demonstrated utility in various reactions including conjugated addition of boronic acids to enones, redox-relay Heck reactions, − Heck–Matsuda arylation, , arylboration, and several Heck-related cascade reactions. , Additionally, the Cu(I) complex of L1 has been employed as a catalytic system for conjugate addition to isocyanoalkenes, Ni(I) complex for hydroalkynylation, and Ni(0) complex for asymmetric reductive coupling . In addition, analogous ligands featuring different substitutions at the oxazoline moiety and maintaining the trifluoromethyl group at the 5-position of the pyridine ring have been employed in various catalytic transformations. − …”

Section: Introductionmentioning

confidence: 99%

“… 13 , 14 Additionally, the Cu(I) complex of L1 has been employed as a catalytic system for conjugate addition to isocyanoalkenes, 15 Ni(I) complex for hydroalkynylation, 16 and Ni(0) complex for asymmetric reductive coupling. 17 In addition, analogous ligands featuring different substitutions at the oxazoline moiety and maintaining the trifluoromethyl group at the 5-position of the pyridine ring have been employed in various catalytic transformations. 18 − 27 …”

Section: Introductionmentioning

confidence: 99%

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Immobilization of Trifluoromethyl-Substituted Pyridine-Oxazoline Ligand and Its Application in Asymmetric Continuous Flow Synthesis of Benzosultams

Kocúrik,

Bartáček,

Drabina

et al. 2023

J. Org. Chem.

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This study presents an improved synthetic route to ligand (S)-4-(tert-butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole and its application as a highly active and enantioselective catalyst in the addition of arylboronic acids to cyclic N-sulfonylketimines. Immobilization of such a ligand was achieved using a commercially available starting material and a PS–PEG TentaGel S NH2 support, resulting in a stable heterogeneous catalyst. Although the anchored catalyst exhibited a slight reduction in enantioselectivity and a 4-fold decrease in reaction rate, it displayed remarkable stability, enabling 10 consecutive reaction cycles. Furthermore, the successful transition to a continuous flow system demonstrated even higher turnover numbers compared to batch arrangements. These findings provide valuable insights into the development of efficient flow reactors for continuous synthesis of benzosultams, further advancing the field of asymmetric catalysis.

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