TY - JOUR
T1 - Development and Mechanistic Study of Quinoline-Directed Acyl C-O Bond Activation and Alkene Oxyacylation Reactions
AU - Hoang, Giang T.
AU - Walsh, Dylan J.
AU - McGarry, Kathryn A.
AU - Anderson, Constance B.
AU - Douglas, Christopher J.
N1 - Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/3/17
Y1 - 2017/3/17
N2 - The intramolecular addition of both an alkoxy and acyl substituent across an alkene, oxyacylation of alkenes, using rhodium catalyzed C-O bond activation of an 8-quinolinyl ester is described. Our unsuccessful attempts at intramolecular carboacylation of ketones via C-C bond activation ultimately informed our choice to pursue and develop the intramolecular oxyacylation of alkenes via quinoline-directed C-O bond activation. We provide a full account of our catalyst discovery, substrate scope, and mechanistic experiments for quinoline-directed alkene oxyacylation.
AB - The intramolecular addition of both an alkoxy and acyl substituent across an alkene, oxyacylation of alkenes, using rhodium catalyzed C-O bond activation of an 8-quinolinyl ester is described. Our unsuccessful attempts at intramolecular carboacylation of ketones via C-C bond activation ultimately informed our choice to pursue and develop the intramolecular oxyacylation of alkenes via quinoline-directed C-O bond activation. We provide a full account of our catalyst discovery, substrate scope, and mechanistic experiments for quinoline-directed alkene oxyacylation.
UR - https://www.scopus.com/pages/publications/85015628968
UR - https://www.scopus.com/inward/citedby.url?scp=85015628968&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.6b03011
DO - 10.1021/acs.joc.6b03011
M3 - Article
C2 - 28252965
AN - SCOPUS:85015628968
SN - 0022-3263
VL - 82
SP - 2972
EP - 2983
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 6
ER -