TY - JOUR
T1 - Dearomative Allylation of Naphthyl Cyanohydrins by Palladium Catalysis
T2 - Catalyst-Enhanced Site Selectivity
AU - Yanagimoto, Aika
AU - Komatsuda, Masaaki
AU - Muto, Kei
AU - Yamaguchi, Junichiro
N1 - Funding Information:
This work was supported by JSPS KAKENHI Grants JP19H02726 (to J.Y.), JP18H04661 (Hybrid Catalysis), and JP19K15573 and The SATOMI Scholarship Foundation (to K.M.). The Materials Characterization Central Laboratory of Waseda University is acknowledged for HRMS measurement.
Publisher Copyright:
© 2020 American Chemical Society.
PY - 2020/5/1
Y1 - 2020/5/1
N2 - A dearomative allylation of naphthyl cyanohydrins with allyl borates and allyl stannanes under palladium catalysis was developed. At the initial stage of this study, the dearomative reaction (C4 substitution of the aromatics) was competing with benzyl substitution. To circumvent this issue, the use of palladium and meta-disubstituted triarylphosphine as the catalyst in a 1:1 ratio was found to enhance the site selectivity, furnishing the desired dearomatized products. Further derivatizations of products were also successful.
AB - A dearomative allylation of naphthyl cyanohydrins with allyl borates and allyl stannanes under palladium catalysis was developed. At the initial stage of this study, the dearomative reaction (C4 substitution of the aromatics) was competing with benzyl substitution. To circumvent this issue, the use of palladium and meta-disubstituted triarylphosphine as the catalyst in a 1:1 ratio was found to enhance the site selectivity, furnishing the desired dearomatized products. Further derivatizations of products were also successful.
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U2 - 10.1021/acs.orglett.0c00897
DO - 10.1021/acs.orglett.0c00897
M3 - Article
C2 - 32272838
AN - SCOPUS:85083213197
SN - 1523-7060
VL - 22
SP - 3423
EP - 3427
JO - Organic Letters
JF - Organic Letters
IS - 9
ER -