Cross‐Coupling Reaction of Alkenyl Sulfoximines and Alkenyl Aminosulfoxonium Salts with Organozincs by Dual Nickel Catalysis and Lewis Acid Promotion

2019 ◽  
Vol 25 (35) ◽  
pp. 8371-8386 ◽  
Author(s):  
Irene Erdelmeier ◽  
Gerd Bülow ◽  
Chang‐Wan Woo ◽  
Jürgen Decker ◽  
Gerhard Raabe ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Nickel Catalysis ◽  
Cross Coupling Reaction

Convergent Synthesis of Immune Inhibitor IMMH002

Synthesis ◽  
2020 ◽  
Author(s):  
Qiong Xiao ◽  
Si Chen ◽  
Zeyu Shi ◽  
Dali Yin
Keyword(s):  
Environmental Impact ◽  
Lewis Acid ◽  
Column Chromatography ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Convergent Synthesis ◽  
Quality Problem ◽  
Cross Coupling Reaction

AbstractA convergent synthesis of IMMH002 in 36% overall yield starting from bromobenzene is described with a key Suzuki–Miyaura cross-coupling reaction used to provide a crucial intermediate. The route does not require column chromatography and solves the most intractable quality problem caused by a homologue by-product in the original linear synthesis. Furthermore, reducing the use of Lewis acid mediated reactions improves the environmental impact of the synthesis and reduces overall waste. The new route described herein is more efficient, convenient, reliable, and economically more viable when compared to the previously reported linear route.

Cross-Coupling Reaction between Alcohols through sp3CH Activation Catalyzed by a Ruthenium/Lewis Acid System

2008 ◽  
Vol 14 (33) ◽  
pp. 10201-10205 ◽  
Author(s):  
Shu-Yu Zhang ◽  
Yong-Qiang Tu ◽  
Chun-An Fan ◽  
Yi-Jun Jiang ◽  
Lei Shi ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Acid System ◽  
Cross Coupling Reaction

scholarly journals Lewis acid-mediated Suzuki–Miyaura cross-coupling reaction

2021 ◽  
Vol 4 (12) ◽  
pp. 1080-1088
Author(s):  
Takashi Niwa ◽  
Yuta Uetake ◽  
Motoyuki Isoda ◽  
Tadashi Takimoto ◽  
Miki Nakaoka ◽  
...  
Keyword(s):  
Controlled Release ◽  
Lewis Acid ◽  
Reliable Method ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Carbon Carbon Bond ◽  
Cross Coupling Reaction ◽  
Theoretical Investigations ◽  
Active Intermediate

AbstractThe palladium-catalysed Suzuki–Miyaura cross-coupling reaction of organohalides and organoborons is a reliable method for carbon–carbon bond formation. This reaction involves a base-mediated transmetalation process, but the presence of a base also promotes competitive protodeborylation. Herein, we established a Suzuki–Miyaura cross-coupling reaction via Lewis acid-mediated transmetalation of an organopalladium(II) intermediate with organoborons. Experimental and theoretical investigations indicate that the controlled release of the transmetalation-active intermediate enables base-independent transmetalation under heating conditions and enhances the applicable scope of this process. This system enables us to avoid the addition of a traditional base and, thus, renders substrates with base-sensitive moieties available. Results from this research further expand the overall utility of cross-coupling chemistry.

Lewis acid-mediated cross-coupling reaction of 7-azaindoles and aldehydes: Cytotoxic evaluation of C3-linked bis-7-azaindoles

2019 ◽  
Vol 60 (34) ◽  
pp. 150974 ◽  
Author(s):  
Suk Hun Lee ◽  
Kunyoung Kim ◽  
Yeong Uk Jeon ◽  
Amit Kundu ◽  
Prasanta Dey ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction
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