Iron chloride hexahydrate-catalyzed Friedel-Crafts akylation of cyclic ketene dithioacetals with alcohols

Abstract

A cost-effective and environmentally compliance FeCl₃·6H₂O catalyzed Friedel-Crafts alkylation of cyclic ketene dithioacetals with alcohols was developed. The reaction was efficient in the presence of catalyst loading as low as 5%(molar fraction) in CH₂Cl₂ solvent at room temperature or under reflux conditions. A wide range of alkylated ketene dithioacetals were synthesized in excellent yields.

Keywords

Iron(III) chloride / Olefin / Ketene dithioacetal / Alcohol / Friedel-Crafts alkylation

References

[1] You S. L., Cai Q., Zeng M. Chem. Soc. Rev., 2009, 38: 2190.

[2] Gao J. R., Wu H., Xiang B., Yu W. B., Han L., Jia Y. X. J. Am. Chem. Soc., 2013, 135: 2983.

[3] Zhai C. W., Xing D., Jing C. C., Zhou J., Wang C. J., Wang D. W., Hu W. H. Org. Lett., 2014, 16: 2934.

[4] Li C., Guo F. F., Xu K., Zhang S., Hu Y. B., Zha Z. G., Wang Z. Y. Org. Lett., 2014, 16: 3192.

[5] Matuszek K., Chrobok A., Hogg J. M., Coleman F., Swadźba-Kwaśny M. Green Chem., 2015, 17: 4255.

[6] Guillena G., Ramón D. J., Yus M. Angew. Chem. Int. Ed., 2007, 46: 2358.

[7] Tsoung J., Krämer K., Zajdlik A., Liébert C., Lautens M. J. Org. Chem., 2011, 76: 9031.

[8] Liébert C., Brinks M. K., Capacci A. G., Fleming M. J., Lautens M. Org. Lett., 2011, 13: 3000.

[9] Nokami T., Yamane Y., Oshitani S., Kobayashi J., Matsui S., Nishihara T., Uno H., Hayase S., Itoh T. Org. Lett., 2015, 17: 3182.

[10] Pan L., Liu Q. Synlett., 2011, 8: 1073.

[11] Pan L., Bi X. H., Liu Q. Chem. Soc. Rev., 2013, 42: 1251.

[12] Yu H. F., Yu Z. K. Angew. Chem. Int. Ed., 2009, 48: 2929.

[13] Yu H. F., Jin W. W., Sun C. L., Yu Z. K. Angew. Chem. Int. Ed., 2010, 49: 5792.

[14] Liu Y., Barry B. D., Yu H. F., Liu J. Q., Liao P. Q., Bi X. H. Org. Lett., 2013, 15: 2608.

[15] Fang Z. X., Liu Y., Barry B. D., Liao P. Q., Bi X. H. Org. Lett., 2015, 17: 782.

[16] Bi X. H., Dong D. W., Liu Q. J. Am. Chem. Soc., 2005, 127: 4578.

[17] Zhang L., Liang F. S., Cheng X., Liu Q. J. Org. Chem., 2009, 74: 899.

[18] Ming W. B., Liu X. C., Wang L. J., Liu J., Wang M. Org. Lett., 2015, 17: 1746.

[19] Luo H. M., Pan L., Xu X. X., Liu Q. J. Org. Chem., 2015, 80: 8282.

[20] Jin W. W., Du W. M., Yang Q., Yu H. F., Yu Z. K. Org. Lett., 2011, 13: 4272.

[21] Dong Y., Wang M., Liu J. Chem. Commun., 2011, 47: 7380.

[22] Yu H. F., Wang D. L., Zhao H., Hou D. Y. Chin. J. Org. Chem., 2011, 31: 1949.

[23] Yu H. F. Chin. J. Chem., 2012, 23: 367.

[24] Yu H. F., Liao P. Q. Chem. J. Chinese Universities, 2012, 33(9): 1969.

[25] Yu H. F. Synth. Commun., 2013, 43: 1280.

[26] Yu H. F., Liao P. Q. Chemistry, 2013, 5: 435.

[27] Zhang Q., Sun S. G., Hu J. L., Liu Q., Tan J. J. Org. Chem., 2007, 72: 139.

[28] Liang D., Wang M., Bekturhun B., Xiong B., Liu Q. Adv. Synth. Catal., 2010, 352: 1593.

[29] Song J. N., Fang Z. X., Liu Y., Li R., Xu L. X., Barry B. D., Liu Q., Bi X. H., Liao P. Q. Synlett., 2011, 2551.

[30] Sperança A., Godoi B., Zeni G. J. Org. Chem., 2013, 78: 1630.

[31] Yang Q., Wu P., Chen J. P., Yu Z. K. Chem. Commun., 2014, 50: 6337.

[32] Mantovani A. C., Goulart T. A. C., Back D. F., Henrique-Menezes P., Zeni G. J. Org. Chem., 2014, 79: 10526.

[33] Bilheri F. N., Stein A. L., Zeni G. Adv. Synth. Catal., 2015, 357: 1221.

[34] Yu H. F., Li T. C., Liao P. Q. Synthesis, 2012, 3743.

[35] Zhao H., Zhang F. W., Yu H. F., Liao P. Q., Diao Q. P., Li T. C., Xin G., Hou D. Y. Chin. J. Org. Chem., 2015, 35: 1493.