Tin tetrachloride-catalyzed regiospecific allylic substitution of quinone monoketals: An easy entry to benzofurans and coumestans

Advanced Synthesis and Catalysis

Volumn 354, Issue 14-15, 2012, Pages 2678-2682

  Liu, Yingjie ^a   Liu, Jingxin ^a   Wang, Mang ^a,b   Liu, Jun ^a   Liu, Qun ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

^b DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Allylic substitution; Cycloaddition; Heterocycles; Quinone monoketals; Regioselectivity

Indexed keywords

EID: 84869013214     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201200344     Document Type: Article

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39. 13C NMR (125 MHz, CDCl3) for 1a: d=185.0, 143.2 (2 C), 129.9 (2 C), 92.4, 50.3 (2 C). The 13C NMR analysis of 1a in the presence of 0.1 equiv. of SnCl4 was performed as follows: to a solution of 1a (39 mg) in 0.5 mL of CDCl3 was added SnCl4 (0.29 ul, 0.1 equiv.). Then, 13C NMR spectra of the resulting solution were recorded at 25 8C on a Varian 125 MHz. It was found that the 13C NMR spectra of 1a in the presence of 0.1 equiv. of SnCl4 were complex. The peaks of dCO and dCACHTUNGTRENUNG(OMe)2 of 1a turned out to be weak and some new peaks, such as those at 187.2 ppm, 157.3 ppm, 136,5 ppm, 99.6 ppm, and 55.5 ppm, were observed. These results show clearly the interactions of both the carbonyl oxygen and methoxy oxygen of 1a with SnCl4 and supported the formation of intermediate A.
40. A comparative reaction between 1a and vinyl sulfide was carried out under identical conditions. However, no reaction was detected with 1 mol% of SnCl4. In the presence of 3 mol% of SnCl4, the reaction gave cycloaddition product 5-methoxy-2-(phenylthio)-2,3-dihydrobenzofuran in 42% yield in 30 min. In addition, we also prepared [2-(4-chlorophenyl)ethene-1,1-diyl]bis(methyl sulfane) to react with 1a under the catalysis of 1 mol% of SnCl4 in MeCN at room temperature. However, no reaction was detected after 3 h at room temperature.