Cobalt-Catalyzed (Hetero)arylation of Saturated Cyclic Amines with Grignard Reagents

Abstract

(Hetero)aryl substituted saturated cyclic amines are ubiquitous scaffolds in biologically active molecules. Metal-catalyzed cross-couplings between halogeno N-heterocycles and organometallic species are efficient and modular reactions to access these attractive scaffolds. An overview of our work concerning the cobalt-catalyzed arylation of iodo-substituted cyclic amines is presented.

Cobalt, copper, and chromium-catalyzed carbon-carbon coupling reactions using a broad spectrum of Grignard reagents as reaction partners

“…[6][7][8][9][10][11][12][13][14][15][16][17] However, alternative cross-coupling protocols must be taken into consideration owing to the high cost of these transition metals, and their limited supply. [18][19][20][21][22][23][24] In addition to this, the development of broadly applicable, more environmental friendly and economical catalysts is a worthy target in catalytic crosscoupling reactions. 25,26 Grignard reagents were discovered, by Victor Grignard at the University of Lyon in 1900, and for this significant finding Grignard was awarded the Nobel Prize in Chemistry in 1912.…”

A One-Pot Iodo-Cyclization/Transition Metal-Catalyzed Cross-Coupling Sequence: Synthesis of Substituted Oxazolidin-2-ones from N-Boc-allylamines

“…Nowadays, the development of methods in organic synthesis is mainly driven by the use of nontoxic, cheap, and earth-abundant metals. For example, in cross-couplings, the replacement of palladium catalysts by metals of the fourth row of the periodic table, such as Fe, Co, Ni, and Cu, is favored. − In the context of our studies on cobalt-catalyzed cross-couplings between alkyl halides and Grignard reagents, we report herein a one-pot iodo-cyclization/cross-coupling sequence to access a diversity of C5-functionalized oxazolidin-2-ones 3 from easily accessible unsaturated N -Boc-allylamines (Scheme ).…”