10.1002/adsc.201900621
Advanced Synthesis & Catalysis
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be efficiently used, thereby making this current
strategy highly valuable for the construction of useful
complex sulfur-containing heterocycles.
Experimental Section
General Considerations:
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1
The H and 13C NMR spectra were recorded in CDCl3
solvents on an NMR spectrometer using TMS as the
internal standard. LRMS was performed on a GC-MS
instrument. HRMS was measured on an electrospray
ionization (ESI) apparatus using time-of-flight (TOF) mass
spectrometry.
Typical Experimental Procedures
Typical Experimental Procedure for the Oxidative
Heteroannulation Reaction of 1,7-Enynes (1) and
Diphenyl disulfide (2a): To a Schlenk tube were added
1,7-enynes 1 (0.2 mmol), diphenyl disulfide 2a (0.1 mmol),
TBPB (1 equiv), Et3N (1 equiv), and DMF (2 mL). Then
o
the tube was charged with argon and was stirred at 60 C
(oil bath temperature) for the indicated time (approximately
12 h) until complete consumption of starting material as
monitored by TLC and/or GC-MS analysis. After the
reaction was finished, the reaction mixture was cooled to
room temperature, diluted in EtOAc (15 mL), and washed
with brine (3×5 mL). The aqueous phase was re-extracted
with EtOAc (3×10 mL). The combined organic extracts
were dried over Na2SO4 and concentrated in vacuum, and
the resulting residue was purified by silica gel column
chromatography (hexane/ethyl acetate = 20:1) to afford the
desired product 3.
Acknowledgements
We thank the National Natural Science Foundation of China (Nos.
21625203 and 21871126) and the Jiangxi Province Science and
Technology Project (Nos. 20171ACB20015 and 20165BCB18007)
for financial support.
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4
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