Et2Zn‐Mediated Gem‐Dicarboxylation of Cyclopropanols with CO2 DOI Creative Commons

Hongjian Liu,

Lei Shi, Xiaobin Tan

et al.

Advanced Science, Journal Year: 2023, Volume and Issue: 11(9)

Published: Dec. 21, 2023

Abstract An unprecedented Et 2 Zn‐mediated gem‐dicarboxylation of C─C/C─H single bond cyclopropanols with CO is disclosed, which provides a straightforward and efficient methodology for the synthesis variety structurally diverse useful malonic acids in moderate to excellent yields. The protocol features mild reaction conditions, functional group compatibility, broad substrate scope, facile derivatization products. DFT calculations confirm that transition‐metal‐free transformation proceeds through novel ring‐opening/ α ‐functionalization/ring‐closing/ring‐opening/ β ‐functionalization (ROFCOF) process, 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) plays dual important roles transformation.

Language: Английский

Palladium‐Catalyzed Carbonylation of Aryl Sulfonium Salts with CO2 as a CO Surrogate DOI
Y. P. Guo, Wei Li, Huanfeng Jiang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(7)

Published: April 9, 2024

Abstract Palladium‐catalyzed carbonylation of aryl sulfonium salts with CO 2 as a surrogate has been successfully developed via one‐pot two‐step procedure. Thus, by merging thianthrenation and the carbonylation, site‐selective aromatic C−H plethora readily available arenes can be realized , providing access to variety structurally diverse useful benzamides, esters carboxylic acids. Simple operation, broad substrate scope, good functional group tolerance mild reaction conditions are attractive features method. Late‐stage functionalization complex bioactive molecules well precise synthesis pharmaceuticals 1‐BCP butoxycaine demonstrated potential application established protocol.

Language: Английский

Citations

3
Ring Transformation of Cyclopropenes to Benzo‐Fused Five‐Membered Oxa‐ and Aza‐Heterocycles via a Formal [4+1] Cyclization DOI Creative Commons

Fengyan Gu,

Binyan Lin,

Zhi‐Huan Peng

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: 11(40)

Published: Aug. 29, 2024

Abstract In the context of growing importance heterocyclic compounds across various disciplines, numerous strategies for their construction have emerged. Exploiting distinctive properties cyclopropenes, this study introduces an innovative approach synthesis benzo‐fused five‐membered oxa‐ and aza‐heterocycles through a formal [4+1] cyclization subsequent acid‐catalyzed intramolecular O ‐ to N rearrangement. These transformations exhibit mild reaction conditions wide substrate scope. The applications in late‐stage modification complex molecules potential PD‐L1 gene down‐regulator, make method highly appealing related fields. Combined experimental mechanistic studies DFT calculations demonstrate Rh(III)‐mediated sequential C─H coupling/π‐allylation/dynamically favorable ‐attack route.

Language: Английский

Citations

1
Et2Zn‐Mediated Gem‐Dicarboxylation of Cyclopropanols with CO2 DOI Creative Commons

Hongjian Liu,

Lei Shi, Xiaobin Tan

et al.

Advanced Science, Journal Year: 2023, Volume and Issue: 11(9)

Published: Dec. 21, 2023

Abstract An unprecedented Et 2 Zn‐mediated gem‐dicarboxylation of C─C/C─H single bond cyclopropanols with CO is disclosed, which provides a straightforward and efficient methodology for the synthesis variety structurally diverse useful malonic acids in moderate to excellent yields. The protocol features mild reaction conditions, functional group compatibility, broad substrate scope, facile derivatization products. DFT calculations confirm that transition‐metal‐free transformation proceeds through novel ring‐opening/ α ‐functionalization/ring‐closing/ring‐opening/ β ‐functionalization (ROFCOF) process, 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) plays dual important roles transformation.

Language: Английский

Citations

3