Flow microreactor synthesis of disubstituted pyridines from dibromopyridines via Br/Li exchange without using cryogenic conditions

…, S Yamada, M Doi, Y Tomida, N Takabayashi…

Index: Nagaki, Aiichiro; Yamada, Shigeyuki; Doi, Masatomo; Tomida, Yutaka; Takabayashi, Naofumi; Yoshida, Jun-Ichi Green Chemistry, 2011 , vol. 13, # 5 p. 1110 - 1113

Full Text: HTML

Citation Number: 28

Abstract

A flow microreactor method for the synthesis of disubstituted pyridines by generation of pyridyllithiums followed by reactions with electrophiles has been developed. By using a short residence time and efficient temperature control, the cryogenic conditions required for conventional batch macro processes can be avoided. Sequential introduction of two different electrophiles into dibromopyridines has been achieved using an integrated flow ...

Related Articles:

Synthesis of a muscarinic receptor antagonist via a diastereoselective Michael reaction, selective deoxyfluorination and aromatic metal-halogen exchange reaction

[Mase; Houpis; Akao; Dorziotis; Emerson; Hoang; Iida; Itoh; Kamei; Kato; Kawasaki; Lang; Lee; Lynch; Maligres; Molina; Nemoto; Okada; Reamer; Song; Tschaen; Wada; Zewge; Volante; Reider; Tomimoto Journal of Organic Chemistry, 2001 , vol. 66, # 20 p. 6775 - 6786]

A facile bromination of hydroxyheteroarenes

[Kato, Yoshiaki; Okada, Shigemitsu; Tomimoto, Koji; Mase, Toshiaki Tetrahedron Letters, 2001 , vol. 42, # 29 p. 4849 - 4851]

Silyl??Mediated Halogen/Halogen Displacement in Pyridines and Other Heterocycles

[Schlosser, Manfred; Cottet, Fabrice European Journal of Organic Chemistry, 2002 , # 24 p. 4181 - 4184]

TMSCH2Li and TMSCH2Li-LiDMAE: Efficient reagents for noncryogenic halogen-lithium exchange in bromopyridines

[Journal of Organic Chemistry, , vol. 72, # 13 p. 4978 - 4980]

One-pot iodination of hydroxypyridines

[Maloney, Kevin M.; Nwakpuda, Emily; Kuethe, Jeffrey T.; Yin, Jingjun Journal of Organic Chemistry, 2009 , vol. 74, # 14 p. 5111 - 5114]

More Articles...