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You‐Jie Yu, Feng‐Lian Zhang, Tianyu Peng, Chang-Ling Wang, Jie Cheng, Chen Chen, Kendall N. Houk, Yi‐Feng Wang
Defluorinative functionalization of readily accessible trifluoromethyl groups constitutes an economical route to partially fluorinated molecules. However, the controllable replacement of one or two fluorine atoms while maintaining high chemoselectivity remains a formidable challenge. Here we describe a general strategy for sequential carbon-fluorine (C-F) bond functionalizations of trifluoroacetamides and trifluoroacetates. The reaction begins with the activation of a carbonyl oxygen atom by a 4-dimethylaminopyridine-boryl radical, followed by a spin-center shift to trigger the C-F bond scission. A chemoselectivity-controllable two-stage process enables sequential generation of difluoro- and monofluoroalkyl radicals, which are selectively functionalized with different radical traps to afford diverse fluorinated products. The reaction mechanism and the origin of chemoselectivity were established by experimental and computational approaches.
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Yu, Y., Zhang, F., Peng, T., Wang, C.-L., Cheng, J., Chen, C., Houk, K. N., & Wang, Y. (2021). Sequential C–F bond functionalizations of trifluoroacetamides and acetates via spin-center shifts. Science, 371(6535), 1232–1240. https://doi.org/10.1126/science.abg0781
Yu, You‐Jie, et al. "Sequential C–F bond functionalizations of trifluoroacetamides and acetates via spin-center shifts." Science, vol. 371, no. 6535, 2021, pp. 1232–1240, https://doi.org/10.1126/science.abg0781.
Yu, You‐Jie, Feng‐Lian Zhang, Tianyu Peng, Chang-Ling Wang, Jie Cheng, Chen Chen, Kendall N. Houk, and Yi‐Feng Wang. "Sequential C–F bond functionalizations of trifluoroacetamides and acetates via spin-center shifts." Science 371, no. 6535 (2021): 1232–1240. https://doi.org/10.1126/science.abg0781.
Yu Y., Zhang F., Peng T. [и др.] Sequential C–F bond functionalizations of trifluoroacetamides and acetates via spin-center shifts // Science. — 2021. — Vol. 371, № 6535. — P. 1232–1240. — URL: https://doi.org/10.1126/science.abg0781
@article{yu2021sequential,
title = {{Sequential C–F bond functionalizations of trifluoroacetamides and acetates via spin-center shifts}},
author = {You‐Jie Yu and Feng‐Lian Zhang and Tianyu Peng and Chang-Ling Wang and Jie Cheng and Chen Chen and Kendall N. Houk and Yi‐Feng Wang},
journal = {Science},
year = {2021},
volume = {371},
number = {6535},
pages = {1232--1240},
doi = {10.1126/science.abg0781},
url = {https://doi.org/10.1126/science.abg0781}
}TY - JOUR AU - Yu, You‐Jie AU - Zhang, Feng‐Lian AU - Peng, Tianyu AU - Wang, Chang-Ling AU - Cheng, Jie AU - Chen, Chen AU - Houk, Kendall N. AU - Wang, Yi‐Feng TI - Sequential C–F bond functionalizations of trifluoroacetamides and acetates via spin-center shifts JO - Science VL - 371 IS - 6535 SP - 1232 EP - 1240 PY - 2021 DA - 2021/03/05 DO - 10.1126/science.abg0781 UR - https://doi.org/10.1126/science.abg0781 ER -
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