Cross‐Coupling of Secondary Amides with Tertiary Amides: The Use of Tertiary Amides as Surrogates of Alkyl Carbanions for Ketone Synthesis

2019 ◽  
Vol 37 (9) ◽  
pp. 887-891 ◽  
Author(s):  
Shu‐Ren Wang ◽  
Pei‐Qiang Huang
Keyword(s):  
Cross Coupling ◽  
Tertiary Amides ◽  
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...

Spectroscopic studies of the electrophilic activation of amides with triflic anhydride and pyridine

2001 ◽  
Vol 79 (11) ◽  
pp. 1694-1703 ◽  
Author(s):  
André B Charette ◽  
Michel Grenon
Keyword(s):  
Spectroscopic Studies ◽  
Initial Reaction ◽  
Spectroscopic Techniques ◽  
Nmr Study ◽  
Acidic Conditions ◽  
Electrophilic Activation ◽  
Tertiary Amides ◽  
Secondary Amides

The reaction of amides with trifluoromethanesulfonic (triflic) anhydride in the presence of pyridine was thoroughly investigated by NMR spectroscopic techniques. Different pyridinium intermediates were generated from secondary amides, tertiary amides with enolizable protons, and tertiary amides lacking enolizable protons. It was found that the actual triflating reagent is N-(trifluoromethylsulfonyl)pyridinium triflate 11 which is formed by the initial reaction of triflic anhydride with pyridine. The alcoholysis of these intermediates yields O-alkyliminium ethers which can then be easily hydrolyzed under mild acidic conditions to the corresponding esters.Key Words: amides, triflic anhydride, pyridinium intermediates, NMR study.

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.

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

scholarly journals Understanding the remarkable difference in liquid crystal behaviour between secondary and tertiary amides: the synthesis and characterisation of new benzanilide-based liquid crystal dimers.

2021 ◽  
Author(s):  
Corrie T. Imrie ◽  
Grant James Strachan ◽  
William T. Harrison ◽  
John M. D. Storey
Keyword(s):  
Liquid Crystal ◽  
Remarkable Difference ◽  
Nematic Phases ◽  
Tertiary Amides ◽  
Secondary Amides

A number of liquid crystal dimers have been synthesised and characterised containing secondary or tertiary (N-methyl) benzanilide-based mesogenic groups. The secondary amides all form nematic phases, and we present the...

Total synthesis of complex alkaloids by nucleophilic addition to amides

2018 ◽  
Vol 16 (21) ◽  
pp. 3864-3875 ◽  
Author(s):  
Takaaki Sato ◽  
Makoto Yoritate ◽  
Hayato Tajima ◽  
Noritaka Chida
Keyword(s):  
Total Synthesis ◽  
Nucleophilic Addition ◽  
Recent Progress ◽  
Nucleophilic Additions ◽  
Tertiary Amides ◽  
Secondary Amides

This mini review focuses on the recent progress of total synthesis of complex alkaloids based on the nucleophilic additions toN-alkoxyamides, tertiary amides and secondary amides.

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
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