Convenient and Direct Azidation of sec-Benzyl Alcohols by Trimethylsilyl Azide with Bismuth(III) Triflate Catalyst

Abstract

sec-Benzyl azides were efficiently prepared by bismuth(III)-catalyzed direct azidation of sec-benzyl alcohols. The reaction was applied to a variety of substrates to provide the desired products in up to 99% yield within a short reaction time.

Key words

azides - catalysis - bismuth - alcohols

• References

• 1a Nui Y.-N, Yan Z.-Y, Gao G.-L, Wang H.-L, Shu X.-Z, Ji K.-G, Liang Y.-M. J. Org. Chem. 2009; 74: 2893
• 1b Huo Z, Yamamoto Y. Tetrahedron Lett. 2009; 50: 3651
• 1c Fischer D, Tomeba H, Pahadi NK, Patil NT, Yamamoto Y. Angew. Chem. Int. Ed. 2007; 46: 4764
• 1d Fischer D, Tomeba H, Pahadi NK, Patil NT, Huo Z, Yamamoto Y. J. Am. Chem. Soc. 2008; 130: 15720
• 2a Lee JG, Choi KI, Koh HY, Kim Y, Kang Y, Cho YS. Synthesis 2001; 81
• 2b Bosch I, Costa AM, Martín M, Urpí F, Vilarrasa J. Org. Lett. 2000; 2: 397
• 3a Hansen SG, Jensen HH. Synlett 2009; 3275
• 3b Hiroki H, Ogata K, Fukuzawa S.-i. Synlett 2013; 24: 843
• 3c Yamada YM. A, Sarkar SM, Uozumi Y. J. Am. Chem. Soc. 2012; 134: 9285
• 4a Gorin D, Davis NR, Toste FD. J. Am. Chem. Soc. 2005; 127: 11260
• 4b Treece JL, Goodell JR, Velde DV, Porco JA. Jr, Aubé J. J. Org. Chem. 2010; 75: 2028
• 5 Desai P, Schildknegt K, Agrios KA, Mossman C, Milligan GL, Aubé J. J. Am. Chem. Soc. 2000; 122: 7226
• 6 Tummatorn J, Thongsornkleeb C, Ruchirawat S. Tetrahedron 2012; 68: 4732
• 7 Tummatorn J, Thongsornkleeb C, Ruchirawat S, Gettongsong T. Org. Biomol. Chem. 2013; 11: 1463
• 8 Tummatorn J, Krajangsri S, Norseeda K, Thongsornkleeb C, Ruchirawat S. Org. Biomol. Chem. 2014; 12: 5077
• 9a Alvarez SG, Alvarez MT. Synthesis 1997; 413
• 9b Zheng H, McDonald R, Hall DG. Chem. Eur. J. 2010; 16: 5454
• 10a Kumar HM. S, Reddy BV. S, Anjaneyulu S, Yadav JS. Tetrahedron Lett. 1998; 39: 7385
• 10b Sreekumar R, Padmakumarband R, Rugmini P. Chem. Commun. 1997; 1133
• 11 Thompson AS, Humphrey GR, DeMarco AH, Mathre DJ, Grabowski EJ. J. J. Org. Chem. 1993; 58: 5886
• 12 Mizuno M, Shioiri T, Mizuno M. Chem. Commun. 1997; 2165
• 13 Kitamura M, Koga T, Yano M, Okauchi T. Synlett 2012; 23: 1335
• 14a Kumar A, Sharma RK, Singh TV, Venugopalan P. Tetrahedron 2013; 69: 10724
• 14b Rueping M, Vila C, Uria U. Org. Lett. 2012; 14: 768
• 14c Khedar P, Pericherla K, Kumar A. Synlett 2014; 25: 515
• 15a Sawama Y, Nagata S, Yabe Y, Morita K, Monguchi Y, Sajiki H. Chem. Eur. J. 2012; 18: 16608
• 15b Sawama Y, Goto R, Nagata S, Shishido Y, Monguchi Y, Sajiki H. Chem. Eur. J. 2014; 20: 2631
• 15c Chan LY, Kim S, Chung WT, Long C, Kim S. Synlett 2011; 415
• 16a Noji M, Ohno T, Fuji K, Futaba N, Tajima H, Ishii K. J. Org. Chem. 2003; 68: 9340
• 16b Chénard E, Hanessian S. Org. Lett. 2014; 16: 2668
• 16c Noji M, Konno Y, Ishii K. J. Org. Chem. 2007; 72: 5161
• 16d Rubenbauer P, Bach T. Tetrahedron Lett. 2008; 49: 1305