TY - JOUR
T1 - Deoxygenative Insertion of Carbonyl Carbon into a C(sp3)-H Bond
T2 - Synthesis of Indolines and Indoles
AU - Asako, Sobi
AU - Ishihara, Seina
AU - Hirata, Keiya
AU - Takai, Kazuhiko
N1 - Funding Information:
We thank MEXT for financial support (KAKENHI Grant-in-Aid for Scientific Research (A) No. 26248030 and No. 18H03911 to K.T. and Grant-in-Aid for Young Scientists (B) No. 15K21180 and Challenging Research (Exploratory) No. 17K19122 to S.A.). We are grateful to Dr. Masahito Murai for X-ray crystal structure analysis.
Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/6/26
Y1 - 2019/6/26
N2 - A simple deoxygenation reagent prepared in situ from commercially available Mo(CO)6 and ortho-quinone has been developed for the synthesis of indoline and indole derivatives. The Mo/quinone complex efficiently deoxygenates carbonyl compounds bearing a neighboring dialkylamino group and effects intramolecular cyclizations with the insertion of a deoxygenated carbonyl carbon into a C(sp3)-H bond, in which a carbonyl group acts as a carbene equivalent. The reaction also proceeds with a catalytic amount of Mo/quinone in the presence of disilane as an oxygen atom acceptor.
AB - A simple deoxygenation reagent prepared in situ from commercially available Mo(CO)6 and ortho-quinone has been developed for the synthesis of indoline and indole derivatives. The Mo/quinone complex efficiently deoxygenates carbonyl compounds bearing a neighboring dialkylamino group and effects intramolecular cyclizations with the insertion of a deoxygenated carbonyl carbon into a C(sp3)-H bond, in which a carbonyl group acts as a carbene equivalent. The reaction also proceeds with a catalytic amount of Mo/quinone in the presence of disilane as an oxygen atom acceptor.
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U2 - 10.1021/jacs.9b05428
DO - 10.1021/jacs.9b05428
M3 - Article
C2 - 31184481
AN - SCOPUS:85068118622
VL - 141
SP - 9832
EP - 9836
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 25
ER -