TY - JOUR
T1 - Ruthenium-catalyzed O- to S-alkyl migration
T2 - a pseudoreversible Barton-McCombie pathway
AU - Mahy, William
AU - Plucinski, Pawel
AU - Jover, Jesús
AU - Frost, Christopher G.
PY - 2015/9/7
Y1 - 2015/9/7
N2 - A practical ruthenium-catalyzed O- to S-alkyl migration affords structurally diverse thiooxazolidinones in excellent yields. Our studies suggest this catalytic transformation proceeds through a pseudoreversible radical pathway drawing mechanistic parallels to the classic Barton-McCombie reaction. A radical step in a new direction: A practical ruthenium-catalyzed O- to S-alkyl migration affords structurally diverse thiooxazolidinones in excellent yields. Experimental and computational studies suggest a pseudoreversible radical pathway drawing mechanistic parallels to the classic Barton-McCombie reaction.
AB - A practical ruthenium-catalyzed O- to S-alkyl migration affords structurally diverse thiooxazolidinones in excellent yields. Our studies suggest this catalytic transformation proceeds through a pseudoreversible radical pathway drawing mechanistic parallels to the classic Barton-McCombie reaction. A radical step in a new direction: A practical ruthenium-catalyzed O- to S-alkyl migration affords structurally diverse thiooxazolidinones in excellent yields. Experimental and computational studies suggest a pseudoreversible radical pathway drawing mechanistic parallels to the classic Barton-McCombie reaction.
KW - alkyl migration
KW - Barton-McCombie reaction
KW - catalysis
KW - O-thiocarbamates
KW - pseudoreversible reaction
UR - http://www.scopus.com/inward/record.url?scp=84940723521&partnerID=8YFLogxK
UR - http://dx.doi.org/10.1002/anie.201505280
U2 - 10.1002/anie.201505280
DO - 10.1002/anie.201505280
M3 - Article
AN - SCOPUS:84940723521
SN - 1433-7851
VL - 54
SP - 10944
EP - 10948
JO - Angewandte Chemie International Edition
JF - Angewandte Chemie International Edition
IS - 37
ER -
