Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 5, Pages 3066-3078Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02849
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Funding
- National Natural Science Foundation of China [21772236, 22101303]
- South-Central University for Nationalities (SCUN) [YZZ18009]
- Natural Science Foundation of Hubei Province [2020CFB250]
- Fundamental Research Funds for the Central Universities (SCUN) [CZQ19014]
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A novel strategy for the formation of copper carbene and a Cu(I)-catalyzed cross-coupling protocol for the synthesis of 7-alkynyl cycloheptatrienes have been reported in this study.
Herein, we report a novel strategy for the formation of copper carbene via the cycloisomerization of the pi-alkyne-Cu(I) complex from terminal alkynes and tropylium tetrafluoroborate. Mechanistic studies and DFT calculations indicate that the reaction undergoes the intramolecular cycloisomerization process from the pi-alkyne-Cu(I) complex to afford the copper carbene intermediate, followed by migratory insertion with the second terminal alkyne to afford the barbaralyl-substituted allenyl acid esters. In addition, we develop a mild and highly efficient Cu(I)-catalyzed cross-coupling protocol to synthesize 7-alkynyl cycloheptatrienes that has a broad functional group tolerance and is applicable to the late-stage functionalization of natural products.
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