91633-31-7Relevant articles and documents
B(C6F5)3-catalyzed synthesis of benzylic azides
Wrigley, Michael S.,Barker, Timothy J.
, p. 1771 - 1776 (2017/09/23)
B(C6F5)3 was found to catalyze the reaction between trimethylsilyl azide and benzylic acetates. Secondary and tertiary benzylic acetates were competent substrates in this reaction providing the azide products in moderate t
A concise synthesis of quinolinium, and biquinolinium salts and biquinolines from benzylic azides and alkenes promoted by copper(II) species
Chen, Wei-Chen,Gandeepan, Parthasarathy,Tsai, Chia-Hung,Luo, Ching-Zong,Rajamalli, Pachaiyappan,Cheng, Chien-Hong
, p. 63390 - 63397 (2016/07/19)
A novel copper-promoted multiple aza-[4 + 2] cycloaddition reaction of N-methyleneanilines in situ generated from benzylic azide and alkenes afforded quinolinium salts, biquinolinium salts, biquinolines or substituted quinolines depending on the substitution on the phenyl ring of benzylic azide. The reaction of para substituted benzylic azides and 2 equivalents of alkenes afforded the corresponding substituted quinolinium salts, while benzylic azides without a para substituent provided biquinolinium salts. The copper-promoted cycloaddition reaction also allows biquinoline products to be obtained from ortho-substituted benzylic azides. These reactions work well with both terminal and internal alkenes. Unsymmetrical internal alkene reactions proceed with high regioselectivity. The reaction is likely started by Lewis acidic CuII-assisted rearrangement of benzylic azide to N-methyleneaniline, followed by a [4 + 2] cycloaddition with alkene. Detailed mechanistic studies suggest that the biquinoline and biquinolinium salts are likely formed via radical processes.
Copper triflate: An efficient catalyst for direct conversion of secondary alcohols into azides
Khedar, Poonam,Pericherla, Kasiviswanadharaju,Kumar, Anil
supporting information, p. 515 - 518 (2014/03/21)
A simple, practical, and efficient strategy has been demonstrated for the direct synthesis of organic azides from alcohols using azidotrimethylsilane (TMSN3) as azide source in the presence of copper(II) triflate [Cu(OTf)2]. A variet