Reductive Alkylation of Quinolines to N-Alkyl Tetrahydroquinolines Catalyzed by Arylboronic Acid

2021 ◽  
Author(s):  
Priyanka Adhikari ◽  
Dipanjan Bhattacharyya ◽  
Sekhar Nandi ◽  
Pavan K. Kancharla ◽  
Animesh Das
Keyword(s):  
Reductive Alkylation ◽  
Arylboronic Acid

Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes

2019 ◽  
Author(s):  
Juha Siitonen ◽  
Padmanabha V. Kattamuri ◽  
Muhammed Yousufuddin ◽  
Laszlo Kurti
Keyword(s):  
Total Synthesis ◽  
Acid Catalysts ◽  
Mechanistic Studies ◽  
Arylboronic Acid ◽  
Synthetic Utility ◽  
Acid Catalyzed

Unprotected keto- and aldoximes are readily <i>C</i>-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly-substituted <i>N</i>-alpha-secondary (2°) and tertiary (3°) hydroxylamines. The method’s synthetic utility is demonstrated with the total synthesis of the trace alkaloid <i>N</i>-methyl-euphococcine. Preliminary experimental and computational mechanistic studies point toward the formation of a boroxine as the active allylating species.<br>

Tandem Amidomercuration-Reductive Alkylation of Alkenes. One-Pot Sythesis of Amidic 1,4-Bifunctionalized Compounds

Synthesis ◽  
1984 ◽  
Vol 1984 (10) ◽  
pp. 831-832 ◽  
Author(s):  
J. Barluenga ◽  
L. Ferrera ◽  
C. Nájera ◽  
M. Yus
Keyword(s):  
Reductive Alkylation ◽  
One Pot

scholarly journals A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst

2020 ◽  
Vol 11 (21) ◽  
pp. 5572-5576 ◽  
Author(s):  
Noboru Hayama ◽  
Yusuke Kobayashi ◽  
Eriko Sekimoto ◽  
Anna Miyazaki ◽  
Kiyofumi Inamoto ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Tertiary Amine ◽  
Michael Addition ◽  
Arylboronic Acid ◽  
Unsaturated Carboxylic Acids

An asymmetric thia-Michael addition of arylthiols to α,β-unsaturated carboxylic acids using a thiourea catalyst that bears arylboronic acid and tertiary amine moieties is reported.

Three-component reductive alkylation of 2-hydroxy-1,4-naphthoquinones with lactols

2016 ◽  
Vol 57 (8) ◽  
pp. 864-867 ◽  
Author(s):  
Eliana E. Kim ◽  
Evans O. Onyango ◽  
Jennifer R. Pace ◽  
Timothy M. Abbot ◽  
Liangfeng Fu ◽  
...  
Keyword(s):  
Reductive Alkylation
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