Journal
ACS CATALYSIS
Volume 9, Issue 4, Pages 3730-3736Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b00218
Keywords
C-N bond activation; Sonogashira; cross-coupling; Pd-NHC complex; DFT
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Funding
- National Natural Science Foundation of China (NSFC) [21571087, 21673156]
- Major Projects of Natural Science Research in Jiangsu Province [15KJA150004]
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A protocol for C(sp)-C(sp(2)) bond formation via the Sonogashira coupling reaction involving C-N bond cleavage with aryltrimethylammonium triflate as an electrophilic coupling partner is described in this work. The reactions proceeded well under mild conditions with a stoichiometric ratio of alkyl, aryl, or heteroaryl acetylenes and provided yields of up to 93%. Numerous useful functional groups were tolerated under the reaction conditions. Direct amine alkynylation can be achieved through a onepot process without the isolation of ammonium salt. The protocol can be performed on a gram scale. Density functional theory calculations were performed to investigate the reaction mechanism that involved oxidative addition, alkyne coordination, deprotonation, and reductive elimination, which yielded the cross-coupling product.
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