Cobalt-Catalyzed Preparation of N-Heterocyclic Organozinc Reagents from Heteroaryl Chlorides

Synthesis ◽  
2021 ◽  
Author(s):  
Alexander Kremsmair ◽  
Simon Graßl ◽  
Christoph Joachim Benedikt Seifert ◽  
Edouard Godineau ◽  
Paul Knochel

Various substituted and unsubstituted N-heterocyclic chlorides have been converted into their corresponding organozinc species using zinc dust in the presence of zinc pivalate and 10% CoCl2 in benzonitrile at 25 °C. The resulting heteroarylzinc reagents were obtained in 43–98% yield within 9–48 h and reacted with a range of electrophiles, leading to the functionalized heteroarenes.

2020 ◽  
Vol 22 (24) ◽  
pp. 9712-9718
Author(s):  
Kodai Yamada ◽  
Tomoyuki Yanagi ◽  
Hideki Yorimitsu

1998 ◽  
Vol 39 (20) ◽  
pp. 3189-3192 ◽  
Author(s):  
Hidetoshi Tokuyama ◽  
Satoshi Yokoshima ◽  
Tohru Yamashita ◽  
Tohru Fukuyama

1913 ◽  
Vol 32 ◽  
pp. 12-16
Author(s):  
Alexander Charles Cumming ◽  
E. W. Hamilton Smith

So many papers have appeared on this subject that some apology seems desirable before making an additional contribution. The amount of published work on reduction with sulphurous acid is in itself an indication that many workers have found difficulties. It has been shown that the reduction does not take place in presence of large excess of hydrochloric or sulphuric acid, but the reduction will still occur while the reaction of the solution is strongly acid. On the other hand, Hillebrand (“Analysis of Silicate and Carbonate Rocks,” U.S. Bulletin, 442, p. 113) states if the solution after addition of sulphite is red in colour, it is too alkaline and acid must be added.


2019 ◽  
Vol 58 (40) ◽  
pp. 14245-14249 ◽  
Author(s):  
Matteo Chierchia ◽  
Peilin Xu ◽  
Gabriel J. Lovinger ◽  
James P. Morken

2013 ◽  
Vol 16 (1) ◽  
pp. 154-157 ◽  
Author(s):  
Benjamin N. Rocke ◽  
Kevin B. Bahnck ◽  
Michael Herr ◽  
Sophie Lavergne ◽  
Vincent Mascitti ◽  
...  

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