구리 촉매에 의한 할로젠화 아릴과 아지도 소듐의 선택적 아지드화 및 아민화 반응

백승욱; Seunguk Paik

Applied Chemistry for Engineering, Vol.32, No.2, 224-227, April, 2021

DOI10.14478/ace.2021.1012 Export Citation

구리 촉매에 의한 할로젠화 아릴과 아지도 소듐의 선택적 아지드화 및 아민화 반응

Selective Copper-Catalyzed Azidation and Amination of Aryl Halides with Sodium Azide

백승욱^†

계명대학교 화학공학과

Seunguk Paik^†

Department of Chemical Engineering, Keimyung University, Daegu 42601, Korea

E-mail:

A rapid and selective copper-catalyzed amination of aryl halides with sodium azide was established by using 10 mol % of CuI, and 20 mol % of N,N’-dimethylethylenediamine in DMSO under microwave irradiation for 10 min. The catalytic system with 4-substituted aryl iodides was found to be the most effective leading to a nearly complete conversion.

Keywords:Azidation;Amination;Microwave irradiation;Copper catalyst;Aryl halides

[References]

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Brase S, Gil C, Knepper K, Zimmermann V, Angew. Chem.-Int. Edit., 44, 5188 (2005)
Kutonova KV, Trusova ME, Postnikov PS, Filimonov VD, Parello J, Synthesis, 45, 2706 (2013)
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Paik S, Jung MG, Bull. Korean Chem. Soc., 33, 689 (2012)
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Great caution should be taken during experiments in a microwave since sodium azide has been reported to be decomposed upon heating to above 275 ℃.

[1] Scriven EV, Turnbull K, Chem. Rev., 88, 297 (1988)

[2] Brase S, Gil C, Knepper K, Zimmermann V, Angew. Chem.-Int. Edit., 44, 5188 (2005)

[3] Kutonova KV, Trusova ME, Postnikov PS, Filimonov VD, Parello J, Synthesis, 45, 2706 (2013)

[4] Bunnett JF, Zahler RE, Chem. Rev., 49, 273 (1951)

[5] Andersen J, Madsen U, Bjorkling F, Liang X, Synlett, 14, 2209 (2005)

[6] Ma D, Cai Q, Accounts Chem. Res., 41, 1450 (2008)

[7] Kwong FY, Buchwald SL, Org. Lett., 5, 793 (2003)

[8] Ji P, Atherton JH, Page MI, J. Org. Chem., 77, 7471 (2012)

[9] Zhao H, Fu H, Qiao R, J. Org. Chem., 75, 3311 (2010)

[10] Cho YA, Kim DS, Ahn HR, Canturk B, Molander GA, Ham J, Org. Lett., 11, 4330 (2009)

[11] Markiewiez JT, Wiest O, Helquist P, J. Org. Chem., 75, 4887 (2010)

[12] Monguchi A, Maejima T, Mori S, Maegawa T, Sajika H, Chem. Eur. J., 16, 7372 (2010)

[13] Paik S, Jung MG, Bull. Korean Chem. Soc., 33, 689 (2012)

[14] Ahammed S, Saha A, Ranu BC, J. Org. Chem., 76, 7235 (2011)

[15] Great caution should be taken during experiments in a microwave since sodium azide has been reported to be decomposed upon heating to above 275 ℃.