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Capturing HBCy 2 : Using N,O‐Chelated Complexes of Rhodium(I) and Iridium(I) for Chemoselective Hydroboration
Author(s) -
Drover Marcus W.,
Schafer Laurel L.,
Love Jennifer A.
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.201511448
Subject(s) - hydroboration , chemoselectivity , agostic interaction , alkene , chemistry , rhodium , chelation , aldehyde , borane , iridium , medicinal chemistry , boranes , double bond , adduct , stereochemistry , organic chemistry , catalysis , metal , boron
1,3‐N,O‐chelated complexes of Rh I and Ir I cooperatively and reversibly stabilized the B−H bond of HBCy 2 to afford six‐membered metallaheterocycles (M=Rh ( 7 ) or Ir ( 8 )) having a δ‐[M]⋅⋅⋅H‐B agostic interaction. Treatment of these Shimoi‐type borane adducts 7 or 8 with both an aldehyde and an alkene resulted in chemoselective aldehyde hydroboration and reformation of the 1,3‐N,O‐chelated starting material. The observed chemoselectivity is inverted from that of free HBCy 2 , which is selective for alkene hydroboration.