TY - JOUR
T1 - Synthetic Access to gem-Difluoropropargyl Vinyl Ethers and Their Application to Propargyl Claisen Rearrangement
AU - Okamura, Toshitaka
AU - Koyamada, Kenta
AU - Kanazawa, Junichiro
AU - Miyamoto, Kazunori
AU - Iwabuchi, Yoshiharu
AU - Uchiyama, Masanobu
AU - Kanoh, Naoki
N1 - Funding Information:
This work was partially supported by The Naito Foundation, by a Grant-in-Aid for Scientific Research on the Innovative Area “Frontier Research on Chemical Communications” (No. 18H04603 to N.K.) from The Ministry of Education, Culture, Sports, Science, and Technology of Japan (MEXT), by the Platform Project for Supporting Drug Discovery and Life Science Research (Platform for Drug Discovery, Informatics, and Structural Life Science) (No. JP18am0101100) from the Japan Agency for Medical Research and Development (AMED), by a Grant-in-Aid for JSPS Fellows (No. 172575 to T.O.), and by a Grant-in-Aid for Scientific Research (S) (No. 17H06173 to M.U.) from the Japan Society for the Promotion of Science (JSPS). Allotment of computational resources (Project G19012) HOKUSAI BigWaterfall (RIKEN) is gratefully acknowledged.
Publisher Copyright:
©
PY - 2021/1/15
Y1 - 2021/1/15
N2 - With the increasing importance of fluorine to medicinal chemistry and other areas, methods to access various fluorinated compounds are needed. Herein, we report the synthesis of difluoropropargyl vinyl ethers from ketones and aldehydes using difluoropropargyl bromide dicobalt complexes. We applied difluoropropargyl vinyl ethers to the synthesis of difluorodienone or difluoroallene under thermal conditions and trifluoro-pyran under acid-catalyzed conditions.
AB - With the increasing importance of fluorine to medicinal chemistry and other areas, methods to access various fluorinated compounds are needed. Herein, we report the synthesis of difluoropropargyl vinyl ethers from ketones and aldehydes using difluoropropargyl bromide dicobalt complexes. We applied difluoropropargyl vinyl ethers to the synthesis of difluorodienone or difluoroallene under thermal conditions and trifluoro-pyran under acid-catalyzed conditions.
UR - http://www.scopus.com/inward/record.url?scp=85097911724&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85097911724&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.0c01777
DO - 10.1021/acs.joc.0c01777
M3 - Article
AN - SCOPUS:85097911724
SN - 0022-3263
VL - 86
SP - 1911
EP - 1924
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -