Enantioselective Difunctionalization of Alkenes by a Palladium‐Catalyzed Heck/Sonogashira Sequence DOI
Lujia Zhou,

Sanliang Li,

Bing Xu

et al.

Angewandte Chemie, Journal Year: 2019, Volume and Issue: 132(7), P. 2791 - 2797

Published: Nov. 22, 2019

Abstract Sonogashira‐type cross‐couplings are one of the most significant alkynylations in organic chemistry. One first palladium‐catalyzed intramolecular Heck/Sonogashira reactions alkenes with terminal alkynes is now reported. With this method, a variety uniquely substituted chiral benzene‐fused heterocycles bearing propargyl‐substituted all‐carbon quaternary stereocenter were obtained straightforward, high‐yielding, and highly stereoselective manner under mild conditions. Salient features process include use readily available substrates, high selectivities, broad substrate scope as well versatile product functionalizations.

Language: Английский

Pd/Xiang-Phos-catalyzed enantioselective intermolecular carboheterofunctionalization under mild conditions DOI Creative Commons

Mengna Tao,

Youshao Tu,

Yu Liu

et al.

Chemical Science, Journal Year: 2020, Volume and Issue: 11(24), P. 6283 - 6288

Published: Jan. 1, 2020

A highly chemo-, regio-, enantio-selectivitive Pd/Xiang-Phos-catalyzed intermolecular carboheterofunctionalization of 2,3-dihydrofurans for the synthesis polysubstituted benzofused heterocycles mild conditions.

Language: Английский

Citations

37

SadPhos Library: A Comprehensive Resource for Exploring Chiral Ligand Chemical Space DOI
Shuang Yu

Chemistry - An Asian Journal, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

Abstract Traditionally, the discovery of ligands for organic reactions has relied heavily on intuition and experience chemists, leading to a trial‐and‐error process that is both time‐consuming inherently biased. The rise data science now offers more systematic efficient approach exploring chemical spaces, moving beyond heuristic constraints conventional ligand design enabling data‐driven, predictive method. In this study, we introduce “SadPhos Library”, comprehensive collection 890 reported chiral sulfinamide phosphine ligands, use physical descriptors systematically map their space. By examining small dataset known active demonstrate how SadPhos library can help identify key properties associated with performance thus streamline optimization. Furthermore, employing dimensionality reduction clustering techniques, pinpoint representative subset facilitates targeted exploration diverse landscape.

Language: Английский

Citations

0

Chiral N,N Ligands Enabling Palladium‐Catalyzed Enantioselective Intramolecular Heck–Matsuda Carbonylation Reactions by Sequential Migratory and CO Insertions DOI
Rafaela C. Carmona, Otto Daolio Köster, Carlos Roque D. Correia

et al.

Angewandte Chemie, Journal Year: 2018, Volume and Issue: 130(37), P. 12243 - 12246

Published: July 19, 2018

Abstract Unprecedented enantioselective intramolecular Heck carbonylation reactions of arenediazonium salts were enabled by a chiral N,N ligand. This reaction constitutes the first that proceeds through migratory insertion followed CO insertion. The enantioenriched functionalized dihydrobenzofurans obtained in good to high yields and enantiomeric ratios up 98:2 under mild operationally simple conditions.

Language: Английский

Citations

35

Asymmetric Reductive and Alkynylative Heck Bicyclization of Enynes to Access Conformationally Restricted Aza[3.1.0]bicycles DOI
Xiaolei Huang,

Minh Hieu Nguyen,

Maoping Pu

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(27), P. 10814 - 10818

Published: March 26, 2020

Conformationally restricted azabicycles are becoming increasingly important in medicinal research. Asymmetric Heck bicyclization of enynes proceeds to give medicinally useful aza[3.1.0] and aza[4.1.0] bicycles with excellent enantioselectivity. The key organopalladium species after can be trapped by silanes terminal alkynes.

Language: Английский

Citations

27

Enantioselective Difunctionalization of Alkenes by a Palladium‐Catalyzed Heck/Sonogashira Sequence DOI
Lujia Zhou,

Sanliang Li,

Bing Xu

et al.

Angewandte Chemie, Journal Year: 2019, Volume and Issue: 132(7), P. 2791 - 2797

Published: Nov. 22, 2019

Abstract Sonogashira‐type cross‐couplings are one of the most significant alkynylations in organic chemistry. One first palladium‐catalyzed intramolecular Heck/Sonogashira reactions alkenes with terminal alkynes is now reported. With this method, a variety uniquely substituted chiral benzene‐fused heterocycles bearing propargyl‐substituted all‐carbon quaternary stereocenter were obtained straightforward, high‐yielding, and highly stereoselective manner under mild conditions. Salient features process include use readily available substrates, high selectivities, broad substrate scope as well versatile product functionalizations.

Language: Английский

Citations

26