scholarly journals Radical zinc-atom-transfer-based carbozincation of haloalkynes with dialkylzincs

2013 ◽  
Vol 9 ◽  
pp. 236-245 ◽  
Author(s):  
Fabrice Chemla ◽  
Florian Dulong ◽  
Franck Ferreira ◽  
Alejandro Pérez-Luna

The formation of alkylidenezinc carbenoids by 1,4-addition/carbozincation of dialkylzincs or alkyl iodides based on zinc atom radical transfer, in the presence of dimethylzinc with β-(propargyloxy)enoates having pendant iodo- and bromoalkynes, is disclosed. Formation of the carbenoid intermediate is fully stereoselective at −30 °C and arises from a formal anti-selective carbozincation reaction. Upon warming, the zinc carbenoid is stereochemically labile and isomerizes to its more stable form.

2012 ◽  
Vol 18 (30) ◽  
pp. 9415-9422 ◽  
Author(s):  
Akira Fusano ◽  
Shuhei Sumino ◽  
Satoshi Nishitani ◽  
Takaya Inouye ◽  
Keisuke Morimoto ◽  
...  

Tetrahedron ◽  
1991 ◽  
Vol 47 (32) ◽  
pp. 6171-6188 ◽  
Author(s):  
Dennis P. Curran ◽  
Dooseop Kim

ACS Catalysis ◽  
2016 ◽  
Vol 7 (1) ◽  
pp. 409-412 ◽  
Author(s):  
Yangyang Shen ◽  
Josep Cornella ◽  
Francisco Juliá-Hernández ◽  
Ruben Martin

ChemInform ◽  
2006 ◽  
Vol 37 (33) ◽  
Author(s):  
Takahide Fukuyama ◽  
Satoshi Nishitani ◽  
Takaya Inouye ◽  
Keisuke Morimoto ◽  
Ilhyong Ryu

2021 ◽  
Author(s):  
Samuel Rieder ◽  
Camilo Meléndez ◽  
Fabrice Dénès ◽  
Kleni Mulliri ◽  
Harish Jangra ◽  
...  

The monoalkylation of N-methoxypyridinium salts with alkyl radicals generated from alkenes (via hydroboration with catecholborane), alkyl iodides (via iodine atom transfer) and xanthates is reported. The reaction proceeds under neutral...


2021 ◽  
Author(s):  
Bartosz Górski ◽  
Anne-Laure Barthelemy ◽  
James J. Douglas ◽  
Fabio Juliá ◽  
Daniele Leonori

2008 ◽  
Vol 14 (29) ◽  
pp. 8784-8788 ◽  
Author(s):  
Alejandro Pérez-Luna ◽  
Candice Botuha ◽  
Franck Ferreira ◽  
Fabrice Chemla

2019 ◽  
Vol 21 (14) ◽  
pp. 5586-5590 ◽  
Author(s):  
Wei-Zhi Weng ◽  
Hao Liang ◽  
Run-Zhou Liu ◽  
Yun-Xing Ji ◽  
Bo Zhang

Sign in / Sign up

Export Citation Format

Share Document