N-Aminopyridinium Ylide-Directed, Copper-Promoted Amination of sp2 C–H Bonds | Zendy

Se Hun Kwak | Zendy; Olafs Daugulis | Zendy

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N-Aminopyridinium Ylide-Directed, Copper-Promoted Amination of sp² C–H Bonds

Author(s) -

Se Hun Kwak,

Olafs Daugulis

Publication year - 2019

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.9b01847

Subject(s) - chemistry , copper , denticity , amination , ylide , medicinal chemistry , alcohol , stereochemistry , polymer chemistry , organic chemistry , crystal structure , catalysis

N -Aminopyridinium ylides are used as monodentate directing groups for copper-promoted C-H/N-H coupling of sp 2 C-H bonds with pyrazoles, imidazoles, and sulfonamides. Reactions proceed in fluorinated alcohol solvents at elevated temperatures and require use of 1.3-3 equiv of copper(II) acetate. This appears to be the first method for copper-promoted C-H/N-H coupling directed by a removable monodentate auxiliary in absence of added ligands.

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