Synthesis of Oxazolidinones by Efficient Fixation of Atmospheric CO₂ with Propargylic Amines by using a Silver/1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU) Dual‐Catalyst System

Abstract

This'll fix it: efficient fixation of atmospheric CO(2) has been achieved by the reaction of propargylic amines with a silver/DBU dual-catalyst system. Various oxazolidinones were synthesized in moderate to good yields by using substituted propargylic amines.

Synthesis of Oxazolidin‐2‐ones from Unsaturated Amines with CO2 by Using Homogeneous Catalysis

“…Therefore, is highly challenging but appealing to realize organic transformations that use CO 2 in air. In 2012, with great effort, Yoshida and co‐workers developed an efficient dual AgNO 3 /DBU catalytic system that could promote the synthesis of oxazolidin‐2‐ones from propargylic amines with CO 2 in air (Scheme ) . No reaction was observed in the absence of DBU.…”

Mechanistic Aspects of the Carboxylative Cyclization of Propargylamines and Carbon Dioxide Catalyzed by Gold(I) Complexes Bearing anN-Heterocyclic Carbene Ligand

“…1 Because 2-oxazolidones are versatile intermediates for the production of pharmaceuticals and fine chemicals and are also chiral auxiliaries, the CO 2 -based dehydrative carboxylation of amino alcohols, 2 the cycloaddition of aziridines 3 and the cyclization of alkynyl and alkenyl amines with CO 2 have been explored to construct the five-membered urethane ring structure. [4][5][6][7][8][9][10][11][12][13][14] These effective CO 2 fixation protocols are based on the conversion of thermodynamically less stable carbamic acids generated from amines and CO 2 into robust urethanes. 15 As a part of our research directed toward the development of addition reactions of CO 2 to unsaturated molecules, 14,16 we recently observed that N-heterocyclic carbene-coordinated Au(I) complexes effectively promote the carboxylative cyclization of propargylamines (1) under ambient CO 2 conditions to afford 5-vinylidene-2-oxazolidones (2) (Scheme 1).…”

Upgrading Carbon Dioxide by Incorporation into Heterocycles

“…Several classes of N-nucleophiles, including propargylamines, allylamines, a-allenyl amines, 2-alkynamides, 2,3-allenamides, o-alkynylaniline, 2-aminobenzonitriles, and diamines are effective for the installation of "CO 2 " or "CO" fragments. [23] In 2012, the Yoshida group [24] disclosed the AgNO 3 /DBU (DBU = 1,8-diazabicyclo [5.4.0]undec-7-ene) dual catalyst system using air as CO 2 source (Scheme 3). He worked then as a post-doctoral fellow at Wuhan University (PR China).…”