TY - JOUR
T1 - Palladium-Catalyzed Remote Diborylative Cyclization of Dienes with Diborons via Chain Walking
AU - Kanno, Shota
AU - Kakiuchi, Fumitoshi
AU - Kochi, Takuya
N1 - Funding Information:
This work was supported, in part, by JSPS KAKENHI Grant Numbers 18H01985 (Grant-in-Aid for Scientific Research (B)) and 15KT0069 (Grant-in-Aid for Scientific Research (B)) as well as the Asahi Glass Foundation. S.K. is also grateful to the Keio University Doctoral Student Grant-in-Aid Program.
Publisher Copyright:
©
PY - 2021/11/24
Y1 - 2021/11/24
N2 - A novel method for catalytic remote bismetalation of alkene substrates by the addition of dimetal reagents is accomplished by using chain walking. In the presence of a palladium catalyst, the reaction of various 1,n-dienes and diborons were converted into cyclopentane derivatives with two boryl groups at remote positions via facile regioselective transformation of an unactivated sp3 C-H bond to a C-B bond. Sequential construction of three distant bonds, which is difficult to achieve by any method, was accomplished for the reactions of 1,n-dienes (n ≥ 7).
AB - A novel method for catalytic remote bismetalation of alkene substrates by the addition of dimetal reagents is accomplished by using chain walking. In the presence of a palladium catalyst, the reaction of various 1,n-dienes and diborons were converted into cyclopentane derivatives with two boryl groups at remote positions via facile regioselective transformation of an unactivated sp3 C-H bond to a C-B bond. Sequential construction of three distant bonds, which is difficult to achieve by any method, was accomplished for the reactions of 1,n-dienes (n ≥ 7).
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U2 - 10.1021/jacs.1c09705
DO - 10.1021/jacs.1c09705
M3 - Article
C2 - 34695350
AN - SCOPUS:85118770256
SN - 0002-7863
VL - 143
SP - 19275
EP - 19281
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 46
ER -