TY - JOUR
T1 - Cobalt-Catalyzed Hydroacylative Dimerization of Allenes Leading to Skipped Dienes
AU - Ding, Wei
AU - Ho, Yan King Terence
AU - Okuda, Yasuhiro
AU - Wijaya, Christopher Kevin
AU - Tan, Zheng Hao
AU - Yoshikai, Naohiko
N1 - Funding Information:
We acknowledge the Ministry of Education (Singapore) and Nanyang Technological University (Nos. MOE2016-T2-2-043 and RG114/18) for financial support of this work. This work was also partially supported by JSPS KAKENHI (Grant Nos. JP18H04430 in Middle Molecular Strategy (Y.O.) and JP19K15574 (Y.O.)), Okayama Foundation of Science and Technology (Y.O.), Promotion and Mutual Aid Corporation for Private Schools of Japan (Y.O.), and OUS Research Project (OUS-RP-19-4 to Y.O.). We thank Dr. Yongxin Li (Nanyang Technological University) for his assistance with the X-ray crystallographic analysis.
Publisher Copyright:
Copyright © 2019 American Chemical Society.
PY - 2019/8/2
Y1 - 2019/8/2
N2 - A cobalt-diphosphine catalyst has been found to promote a selective 1:2 coupling reaction between aldehydes and allenes to form β,δ-dialkylidene ketones, featuring skipped diene moieties, with high regioselectivities and stereoselectivities. The reaction is distinct from previously reported, rhodium-catalyzed aldehyde-allene 1:2 coupling to afford β,γ-dialkylidene ketones bearing 1,3-diene moieties. The present hydroacylative dimerization involves a unique allene/allene oxidative cyclization mode to form a C1-C2 linkage between the allene molecules.
AB - A cobalt-diphosphine catalyst has been found to promote a selective 1:2 coupling reaction between aldehydes and allenes to form β,δ-dialkylidene ketones, featuring skipped diene moieties, with high regioselectivities and stereoselectivities. The reaction is distinct from previously reported, rhodium-catalyzed aldehyde-allene 1:2 coupling to afford β,γ-dialkylidene ketones bearing 1,3-diene moieties. The present hydroacylative dimerization involves a unique allene/allene oxidative cyclization mode to form a C1-C2 linkage between the allene molecules.
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U2 - 10.1021/acs.orglett.9b02465
DO - 10.1021/acs.orglett.9b02465
M3 - Article
C2 - 31334661
AN - SCOPUS:85071060061
SN - 1523-7060
VL - 21
SP - 6173
EP - 6178
JO - Organic Letters
JF - Organic Letters
IS - 15
ER -