Copper-Catalyzed C–H Fluorination/Functionalization Sequence Enabling Benzylic C–H Cross Coupling with Diverse Nucleophiles | Zendy

Aristidis Vasilopoulos | Zendy; Dung L. Golden | Zendy; Joshua A. Buss | Zendy; Shan S. Stahl | Zendy

Open Access

Copper-Catalyzed C–H Fluorination/Functionalization Sequence Enabling Benzylic C–H Cross Coupling with Diverse Nucleophiles

Author(s) -

Aristidis Vasilopoulos,

Dung L. Golden,

Joshua A. Buss,

Shan S. Stahl

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c02238

Subject(s) - chemistry , nucleophile , electrophile , catalysis , surface modification , medicinal chemistry , lewis acids and bases , combinatorial chemistry , electrophilic fluorination , fluoride , fluorine , hydrogen bond , organic chemistry , molecule , inorganic chemistry

Site-selective transformation of benzylic C-H bonds into diverse functional groups is achieved via Cu-catalyzed C-H fluorination with N -fluorobenzenesulfonimide (NFSI), followed by substitution of the resulting fluoride with various nucleophiles. The benzyl fluorides generated in these reactions are reactive electrophiles in the presence of hydrogen-bond donors or Lewis acids, allowing them to be used without isolation in C-O, C-N, and C-C coupling reactions.

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