ChemInform Abstract: Selective Formation of Secondary Amides via the Copper-Catalyzed Cross-Coupling of Alkylboronic Acids with Primary Amides.

ChemInform ◽  
2013 ◽  
Vol 44 (36) ◽  
pp. no-no
Author(s):  
Steven A. Rossi ◽  
Kirk W. Shimkin ◽  
Qun Xu ◽  
Luis M. Mori-Quiroz ◽  
Donald A. Watson
Keyword(s):  
Cross Coupling ◽  
Selective Formation ◽  
Secondary Amides

scholarly journals Selective Formation of Secondary Amides via the Copper-Catalyzed Cross-Coupling of Alkylboronic Acids with Primary Amides

2013 ◽  
Vol 15 (9) ◽  
pp. 2314-2317 ◽  
Author(s):  
Steven A. Rossi ◽  
Kirk W. Shimkin ◽  
Qun Xu ◽  
Luis M. Mori-Quiroz ◽  
Donald A. Watson
Keyword(s):  
Cross Coupling ◽  
Selective Formation ◽  
Secondary Amides

Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of C-F Bonds

2021 ◽  
Author(s):  
Tianhao Zhang ◽  
Itsuki Nohira ◽  
Naoto Chatani
Keyword(s):  
Cross Coupling ◽  
Secondary Amides

The efficient Suzuki-Miyaura cross-coupling of ortho-fluoro aromatic secondary amides with aryl boronates is described. The use of KOtBu is essential for the reaction to proceed. The function of the base...

scholarly journals Understanding Site Selectivity in the Palladium-Catalyzed Cross-Coupling of Allenylsilanolates

Synlett ◽  
2017 ◽  
Vol 28 (18) ◽  
pp. 2415-2420
Author(s):  
Scott Denmark ◽  
Andrea Ambrosi
Keyword(s):  
Cross Coupling ◽  
The Other ◽  
Fine Tuning ◽  
Reaction Conditions ◽  
Site Selectivity ◽  
Palladium Catalyzed ◽  
Selective Formation ◽  
Useful Yield

Allenylsilanolates can undergo cross-coupling at the α- or γ-terminus, and site selectivity appears to be determined by the intrinsic transmetalation mechanism. Fine-tuning of concentration, nucleophilicity, and steric bulk of the silanolate moiety allows for the selective formation of one isomer over the other. Whereas the α-isomer can be obtained in synthetically useful yield, the γ-isomer is favored only when employing reaction conditions that are inevitably associated with diminished reactivity.

Direct reductive coupling of secondary amides: chemoselective formation of vicinal diamines and vicinal amino alcohols

2015 ◽  
Vol 51 (6) ◽  
pp. 1096-1099 ◽  
Author(s):  
Pei-Qiang Huang ◽  
Qi-Wei Lang ◽  
Ai-E Wang ◽  
Jian-Feng Zheng
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Amino Alcohols ◽  
Reductive Coupling ◽  
Cross Coupling Reaction ◽  
Carbon Radicals ◽  
Direct Generation ◽  
Homocoupling Reaction ◽  
Reductive Homocoupling ◽  
Secondary Amides

We report the first direct and chemoselective reductive homocoupling reaction of secondary amides and cross-coupling reaction of secondary amides with ketones. This method relies on the direct generation of α-amino carbon radicals from amides.

Manganese-Catalyzed Kumada Cross-Coupling Reactions of Aliphatic Grignard Reagents with N-Heterocyclic Chlorides

Synlett ◽  
2018 ◽  
Vol 29 (13) ◽  
pp. 1700-1706 ◽  
Author(s):  
Ellen Matson ◽  
Brittney Petel ◽  
Merjema Purak
Keyword(s):  
Reaction Rate ◽  
Metal Salt ◽  
Cross Coupling ◽  
Environmentally Benign ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Heterocyclic Molecules ◽  
Cross Coupling Reactions ◽  
High Yields ◽  
Selective Formation

Herein we report the use of manganese(II) chloride for the catalytic generation of C(sp2)–C(sp3) bonds via Kumada cross-coupling. Rapid and selective formation of 2-alkylated N-heterocyclic complexes were observed in high yields with use of 3 mol% MnCl2THF1.6 and under ambient reaction conditions (21 °C, 15 min to 20 h). Manganese-catalyzed cross-coupling is tolerant toward both electron-donating and electron-withdrawing functional groups in the 5-position of the pyridine ring, with the latter resulting in an increased reaction rate and a decrease in the amount of nucleophile required. The use of this biologically and environmentally benign metal salt as a catalyst for C–C bond formation highlights its potential as a catalyst for the late-stage functionalization of pharmaceutically active N-heterocyclic molecules (e.g., pyridine, pyrazine).

Synthesis of functionalised fluorinated pyridine derivatives by site-selective Suzuki-Miyaura cross-coupling reactions of halogenated pyridines

2017 ◽  
Vol 72 (4) ◽  
pp. 263-279 ◽  
Author(s):  
Muhammad Sharif ◽  
Khurram Shoaib ◽  
Shahzad Ahmed ◽  
Sebastian Reimann ◽  
Jamshed Iqbal ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Pyridine Derivatives ◽  
One Pot ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions ◽  
The One ◽  
Site Selective ◽  
Selective Formation

AbstractThe Suzuki-Miyaura reaction of 2,6-dichloro-3-(trifluoromethyl)pyridine with 1 equiv of arylboronic acids resulted in site-selective formation of 2-aryl-6-chloro-3-(trifluoromethyl)pyridine. Due to electronic reasons, the reaction takes place at the sterically more hindered position. The selectivity was rationalised by DFT calculations. The one-pot reaction with two different arylboronic acids afforded 2,6-diaryl-3-(trifluoromethyl)pyridine containing two different aryl substituents. The reactions proceeded smoothly in the absence of phosphine ligands. In addition, Suzuki-Miyaura reactions of 2,6-dichloro-4-(trifluoromethyl)pyridine with one or two equivalents of arylboronic acids were carried out.

Photoredox/Pd dual-catalytic three-component cross-coupling

2020 ◽  
Author(s):  
Logan Forshee ◽  
Kaitie Cartwright ◽  
Jon Tunge ◽  
Megan Hegarty
Keyword(s):  
Cross Coupling
Sign in / Sign up

Export Citation Format

Share Document