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

共 50 条

[1] Reduction of polycyclic aromatic hydrocarbons promoted by cobalt or manganese nanoparticles
Nador, Fabiana
Moglie, Yanina
Vitale, Cristian
Yus, Miguel
Alonso, Francisco
Radivoy, Gabriel
TETRAHEDRON, 2010, 66 (24) : 4318 - 4325
[2] NO decomposition over sodium-promoted cobalt oxide
Park, PW
Kil, JK
Kung, HH
Kung, MC
CATALYSIS TODAY, 1998, 42 (1-2) : 51 - 60
[3] Selective catalytic hydrogenation of polycyclic aromatic hydrocarbons promoted by ruthenium nanoparticles
Breso-Femenia, Emma
Chaudret, Bruno
Castillon, Sergio
CATALYSIS SCIENCE & TECHNOLOGY, 2015, 5 (05) : 2741 - 2751
[4] SODIUM-PROMOTED CLAISEN ESTER CONDENSATIONS OF ETHYL PERFLUOROALKANECARBOXYLATES
BURDON, J
MCLOUGHLIN, VC
TETRAHEDRON, 1964, 20 (10) : 2163 - &
[5] Separation of polycyclic aromatic hydrocarbons with sodium dodecylbenzenesulfonate in electrokinetic chromatography
Kavran, G
Erim, FB
JOURNAL OF CHROMATOGRAPHY A, 2002, 949 (1-2) : 301 - 305
[6] Solubilization of polycyclic aromatic hydrocarbons in aqueous sodium dioctylsulfosuccinate solutions
Srivastava, A.
Ismail, K.
JOURNAL OF MOLECULAR LIQUIDS, 2014, 195 : 105 - 109
[7] SODIUM-PROMOTED CONDENSATION OF ORGANIC HALIDES AND CARBONYL COMPOUNDS
FRANK, CE
FOSTER, WE
INDUSTRIAL AND ENGINEERING CHEMISTRY, 1954, 46 (05): : 1019 - 1021
[8] POLYCYCLIC AROMATIC HYDROCARBONS
COOK, JW
JOURNAL OF THE CHEMICAL SOCIETY, 1950, (APR): : 1210 - 1219
[9] Carborane-arene fused boracyclic analogues of polycyclic aromatic hydrocarbons accessed by intramolecular borylation
Li, Yijie
Tamizmani, Masilamani
Akram, Manjur O.
Martin, Caleb D.
CHEMICAL SCIENCE, 2024, 15 (20) : 7568 - 7575
[10] Synthesis of Boron-Doped Polycyclic Aromatic Hydrocarbons by Tandem Intramolecular Electrophilic Arene Borylation
Miyamoto, Fumiya
Nakatsuka, Soichiro
Yamada, Keitaro
Nakayama, Ken-ichi
Hatakeyama, Takuji
ORGANIC LETTERS, 2015, 17 (24) : 6158 - 6161

← 1 2 3 4 5 →