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Synthesis of CF3-Containing Linear Nitriles from α-(Trifluoromethyl)styrenes

Sixue Xu, Yupian Deng, Jingjing He, Qianding Zeng, Chuan Liu, Yi Zhang, Bin Zhu and Song Cao*

*Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology (ECUST), Shanghai 200237, China, Email: scaoecust.edu.cn

L. Liu, L. Li, X. Wang, R. Sun, M.-D. Zhou, H. Wang, Org. Lett., 2021, 23, 5826-5830.

DOI: 10.1021/acs.orglett.1c01988


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Abstract

Base-catalyzed/mediated nucleophilic additions of TMSCN to α-(trifluoromethyl)styrenes and 2-trifluoromethyl enynes proceeded smoothly at room temperature under mild and transition-metal-free conditions without affecting the trifluoromethyl group to afford the corresponding CF3-containing alkyl, alkynyl, and butadienyl nitriles in good yields in a highly regioselective manner.

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General procedure

To a glass tube charged with a stirring bar were added DBU (159.6 mg, 1.05 mmol, 1.5 equiv), α-trifluoromethylbenzene (0.7 mmol), TMSCN (277.2 mg, 2.8 mmol, 4.0 equiv) and DMF (7 mL). The reaction vial was sealed with a rubber septum and then the reaction mixture was stirred at room temperature for 6 h (monitored by TLC and GC/MS). After the completion of reaction, the reaction mixture was quenched with saturated aqueous solution of NH4Cl (5 mL) and extracted with ethyl acetate (3 10 mL). The organic layer was separated and dried over Na2SO4, filtered and concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel using n-hexane/ethyl acetate (20/1, 10/1, or 3/1) as eluent to afford the pure target compounds.


Key Words

cyanation


ID: J54-Y2021