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Synfacts 2020; 16(12): 1442
DOI: 10.1055/s-0040-1706573
DOI: 10.1055/s-0040-1706573
Metals in Synthesis
Enantioconvergent Coupling of Racemic Alkyl Bromides with Azole C–H Bonds
Su X.-L,
Ye L,
Chen J.-J,
Liu X.-D,
Jiang S.-P,
Wang F.-L,
Liu L,
Yang C.-J,
Chang X.-Y,
Li Z.-L,
Gu Q.-S,
Liu X.-Y.
*
Southern University of Science and Technology, Shenzhen, P. R. of China
Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2)-H Bonds.
Angew. Chem. Int. Ed. 2020;
DOI: 10.1002/anie.202009527
Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2)-H Bonds.
Angew. Chem. Int. Ed. 2020;
DOI: 10.1002/anie.202009527
Significance
The authors report a copper-catalyzed cross-coupling of racemic bromides with azole C–H bonds. The use of a copper(I)/cinchona-alkaloid-derived N,N,P-ligand catalytic system leads to the enantiomerically enriched α-chiral heteroarene products in high enantioselectivity.
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Comment
A mechanism based on experimental studies is proposed. The results indicate the presence of an alkyl radical species. A subsequent transformation of the 1,3,4-oxadiazole products into 1,2,4 triazole is reported.
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Publication History
Article published online:
17 November 2020
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