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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