Alkali Metal–Promoted Facile Synthesis of Secondary Amines from Imines and Carbodiimides

2020 ◽  
Vol 34 (9) ◽  
Author(s):  
Tarun K. Panda ◽  
Indrani Banerjee ◽  
Shweta Sagar
2015 ◽  
Vol 44 (33) ◽  
pp. 14842-14853 ◽  
Author(s):  
Tobias Böttcher ◽  
Cameron Jones

The synthesis of a series of extremely bulky secondary amines with a phosphine function, Ar†(PR2)NH (Ar†= C6H2{C(H)Ph2}2Pri-2,6,4; R = Ph, NEt2, NPri2) is described. Deprotonation with eithern-BuLi or KH yields the respective alkali metal amides. Reactions with a series of chlorosilanes allows access to monomeric molecular compounds bearing the extremely bulky amino substituentsviasalt elimination.


1999 ◽  
Vol 38 (3) ◽  
pp. 496-506 ◽  
Author(s):  
Shinzi Kato ◽  
Nobuyuki Kitaoka ◽  
Osamu Niyomura ◽  
Yuka Kitoh ◽  
Takahiro Kanda ◽  
...  

Synlett ◽  
2019 ◽  
Vol 31 (05) ◽  
pp. 455-458
Author(s):  
Tamal Roy ◽  
Ji-Woong Lee

We report a facile synthesis of sulfones, β-keto sulfones, and sulfonamides from vinyl sulfones via an addition–elimination sequence where in situ generation of nucleophilic sulfinate ion is mediated by cyanide. The use vinyl sulfones renders high selectivity for S-alkylation to produce sulfones in high yields. In the presence of N-bromosuccinimide, primary and secondary amines underwent sulfonamide formation. A preliminary mechanistic study showed the formation of acrylonitrile as an innocent byproduct, without interfering with the desired reaction pathway while generating a sulfinate nucleophile.


2019 ◽  
Vol 131 (9) ◽  
pp. 2746-2750 ◽  
Author(s):  
Xi‐Meng Chen ◽  
Nana Ma ◽  
Xin‐Ran Liu ◽  
Changgeng Wei ◽  
Chong‐Chao Cui ◽  
...  

2003 ◽  
pp. 3365-3369 ◽  
Author(s):  
Klaus Merz ◽  
Stefan Block ◽  
Robert Schoenen ◽  
Matthias Driess

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