Rhodium-catalyzed addition of arylboronic acids to isatins: an entry to diversity in 3-aryl-3-hydroxyoxindoles.
[reaction: see text] A general method for the catalytic 1,2-addition of aryl and alkenyl boronic acids to isatins is described using a rhodium(I)/triphenylphosphite catalyst. The application of this transformation allows the synthesis of a variety of 3-aryl-3-hydroxyoxindole building blocks in high yields. An enantioselective version of this reaction using a rhodium(I)/phosphoramidite system is also presented.
Toullec
Patrick Y
PY
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, The Netherlands.
Jagt
Richard B C
RB
de Vries
Johannes G
JG
Feringa
Ben L
BL
Minnaard
Adriaan J
AJ
D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000031:analogs & derivatives* / Q000737:chemistry*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*
D001897:Boronic Acids; D007211:Indoles; D007510:Isatin; D012238:Rhodium