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Copper‐ and Cobalt‐Catalyzed Syntheses of Thiophene‐Based Tertiary Amines
Author(s) -
Bouarfa Salima,
Graßl Simon,
Ivanova Maria,
Langlais Timothy,
BentabedAbabsa Ghenia,
Lassagne Frédéric,
Erb William,
Roisnel Thierry,
Dorcet Vincent,
Knochel Paul,
Mongin Florence
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900276
Subject(s) - transmetalation , chemistry , amination , halide , catalysis , deprotonation , cobalt , copper , thiophene , medicinal chemistry , organic chemistry , combinatorial chemistry , polymer chemistry , ion
Thienylzinc halides and related compounds prepared by deprotonation followed by transmetalation were used in copper‐catalyzed amination using N ‐benzoyloxy secondary amines. By extending the reaction to 1,5‐naphthyridine, it was showed that the competitive dimer formation observed in the case of thiophenes was linked with the low stability of some thienylamines rather than homocoupling. Interestingly, thienylzinc halides and related compounds prepared by transmetalation of thienylmagnesium halides, either prepared from their bromo‐precursors or generated by deprotometalation, were satisfactorily employed in cobalt‐catalyzed aminations. Finally, aminothiophenes were involved in copper‐catalyzed mono‐ and di‐ N ‐arylations, affording differently substituted di‐ and triphenylamines.