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DOI	10.1126/science.aan1411
	A catalytic fluoride-rebound mechanism for C(sp3)-CF3 bond formation
	Levin M.D.; Chen T.Q.; Neubig M.E.; Hong C.M.; Theulier C.A.; Kobylianskii I.J.; Janabi M.; O'Neil J.P.; Toste F.D.
发表日期	2017
ISSN	0036-8075
起始页码	1272
结束页码	1275
卷号	356 期号:6344
英文摘要	The biological properties of trifluoromethyl compounds have led to their ubiquity in pharmaceuticals, yet their chemical properties have made their preparation a substantial challenge, necessitating innovative chemical solutions. We report the serendipitous discovery of a borane-catalyzed formal C(sp3)-CF3 reductive elimination from Au(III) that accesses these compounds by a distinct mechanism proceeding via fluoride abstraction, migratory insertion, and C-F reductive elimination to achieve a net C-C bond construction. The parent bis(trifluoromethyl)Au(III) complexes tolerate a surprising breadth of synthetic protocols, enabling the synthesis of complex organic derivatives without cleavage of the Au-C bond. This feature, combined with the "fluoride-rebound" mechanism, was translated into a protocol for the synthesis of 18F-radiolabeled aliphatic CF3-containing compounds, enabling the preparation of potential tracers for use in positron emission tomography. © The Authors, some rights reserved.
英文关键词	borane derivative; fluoride; fluorine 18; gold complex; osmium; periodate; fluoride; gold; tracer; carbon isotope; catalysis; catalyst; chemical bonding; chemical compound; drug; fluoride; gold; tracer; Article; catalysis; chemical bond; chemical reaction; column chromatography; cross metathesis; density functional theory; dihydroxylation; drug half life; fluorine nuclear magnetic resonance; high performance liquid chromatography; hydroboration; hydrogenation; hydrolysis; isotope labeling; nitration; nuclear magnetic resonance; nucleophilicity; positron emission tomography; priority journal; purification; radiochemistry; Simmons Smith reaction; synthesis; chemistry; medicinal chemistry; procedures; Boranes; Chemistry Techniques, Synthetic; Chemistry, Pharmaceutical; Fluorides; Gold; Positron-Emission Tomography; Radioactive Tracers; Radiochemistry
语种	英语
来源期刊	Science
文献类型	期刊论文
条目标识符	http://gcip.llas.ac.cn/handle/2XKMVOVA/244514
作者单位	Department of Chemistry, University of California, Berkeley, CA 94720, United States; Chemical Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720, United States; Biomedical Isotope Laboratory, Lawrence Berkeley National Laboratory, Berkeley, CA 94720, United States
推荐引用方式 GB/T 7714	Levin M.D.,Chen T.Q.,Neubig M.E.,et al. A catalytic fluoride-rebound mechanism for C(sp3)-CF3 bond formation[J],2017,356(6344).
APA	Levin M.D..,Chen T.Q..,Neubig M.E..,Hong C.M..,Theulier C.A..,...&Toste F.D..(2017).A catalytic fluoride-rebound mechanism for C(sp3)-CF3 bond formation.Science,356(6344).
MLA	Levin M.D.,et al."A catalytic fluoride-rebound mechanism for C(sp3)-CF3 bond formation".Science 356.6344(2017).