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

页码：4613 / 4617

页数：5

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