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The Multiple Facets of Iodine(III) Compounds in an Unprecedented Catalytic Auto‐amination for Chiral Amine Synthesis
Author(s) -
Buendia Julien,
Grelier Gwendal,
Darses Benjamin,
Jarvis Amanda G.,
Taran Frédéric,
Dauban Philippe
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201602022
Subject(s) - hypervalent molecule , amination , chemistry , catalysis , iodine , amine gas treating , reagent , moiety , aryl , combinatorial chemistry , organic chemistry , palladium , alkyl
Abstract Iodine(III) reagents are used in catalytic one‐pot reactions, first as both oxidants and substrates, then as cross‐coupling partners, to afford chiral polyfunctionalized amines. The strategy relies on an initial catalytic auto C(sp 3 )−H amination of the iodine(III) oxidant, which delivers an amine‐derived iodine(I) product that is subsequently used in palladium‐catalyzed cross‐couplings to afford a variety of useful building blocks with high yields and excellent stereoselectivities. This study demonstrates the concept of self‐amination of the hypervalent iodine reagents, which increases the value of the aryl moiety.