Sodium-Promoted Borylation of Polycyclic Aromatic Hydrocarbons

被引：18
|
作者：
Fukazawa, Mizuki [1 ]
Takahashi, Fumiya [1 ]
Yorimitsu, Hideki [1 ]
机构：
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 12期
关键词：
METAL-AMMONIA REDUCTION; SUBSTITUTED BENZENE-DERIVATIVES; REDOX BEHAVIOR; CATALYZED BORYLATION; AZULENE;
D O I：
10.1021/acs.orglett.1c01355
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Sodium dispersion promotes the reductive borylation of polycyclic aromatic hydrocarbons (PAHs) with MeOBpin. Anthracenes and phenanthrenes are converted to the corresponding dearomatized diborylated products. The reductive diborylation of naphthalene-based small pi-systems yields similar yet unstable products that are oxidized into formal C-H borylation products with unique regioselectivity. Pyrene is converted to 1-borylpyrene without the addition of an oxidant. The latter two reactions represent a new route to useful borylated PAHs that rivals C-X borylation and catalytic C-H borylation.
引用
收藏
页码：4613 / 4617
页数：5
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