Regioselective Formylation of Pyrrole-2-Carboxylate: Crystalline Vilsmeier Reagent vs Dichloromethyl Alkyl Ether

2018 ◽  
Vol 23 (4) ◽  
pp. 614-618 ◽  
Author(s):  
Takuya Warashina ◽  
Daisuke Matsuura ◽  
Tetsuya Sengoku ◽  
Masaki Takahashi ◽  
Hidemi Yoda ◽  
...  
Science ◽  
2021 ◽  
Vol 372 (6538) ◽  
pp. 175-182
Author(s):  
Hairong Lyu ◽  
Ilia Kevlishvili ◽  
Xuan Yu ◽  
Peng Liu ◽  
Guangbin Dong

Mild methods to cleave the carbon-oxygen (C−O) bond in alkyl ethers could simplify chemical syntheses through the elaboration of these robust, readily available precursors. Here we report that dibromoboranes react with alkyl ethers in the presence of a nickel catalyst and zinc reductant to insert boron into the C−O bond. Subsequent reactivity can effect oxygen-to-nitrogen substitution or one-carbon homologation of cyclic ethers and more broadly streamline preparation of bioactive compounds. Mechanistic studies reveal a cleavage-then-rebound pathway via zinc/nickel tandem catalysis.


Cell Calcium ◽  
2021 ◽  
pp. 102435
Author(s):  
Maxime Guéguinou ◽  
Romain Felix ◽  
Séverine Marionneau-Lambot ◽  
Thibault Oullier ◽  
Aubin Penna ◽  
...  

Tetrahedron ◽  
1992 ◽  
Vol 48 (31) ◽  
pp. 6499-6510 ◽  
Author(s):  
Tirumalai R.Kasturi ◽  
Subramaniam Arumugam ◽  
Lata Mathew ◽  
Srirangam K. Jayaram ◽  
parthasarathi Dastidar ◽  
...  

2012 ◽  
Vol 134 (17) ◽  
pp. 7313-7316 ◽  
Author(s):  
Shu-Yu Zhang ◽  
Gang He ◽  
Yingsheng Zhao ◽  
Kiwan Wright ◽  
William A. Nack ◽  
...  

2013 ◽  
Vol 27 (6) ◽  
pp. 3122-3129 ◽  
Author(s):  
Ziyu Liu ◽  
Lei Zhang ◽  
Xulong Cao ◽  
Xinwang Song ◽  
Zhiqiang Jin ◽  
...  

Lipids ◽  
1980 ◽  
Vol 15 (6) ◽  
pp. 475-478 ◽  
Author(s):  
Takayuki Sugiura ◽  
Yasuo Masuzawa ◽  
Keizo Waku

2015 ◽  
Author(s):  
G. Alvarez Jürgenson ◽  
C. Bittner ◽  
V. Kurkal-Siebert ◽  
G. Oetter ◽  
J. Tinsley

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