Catalyst- and solvent-free ipso-hydroxylation of arylboronic acids to phenols

被引：20

作者：

Yang, Xiufang ^{[1
,2
]}

Jiang, Xulu ^{[1
]}

Wang, Weitao ^{[1
,2
]}

Yang, Qi ^{[3
]}

Ma, Yangmin ^{[1
,2
]}

Wang, Kuan ^{[1
,2
]}

机构：

[1] Shaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Xian 710021, Shaanxi, Peoples R China

[2] Shaanxi Univ Sci & Technol, Shaanxi Key Lab Chem Addit Ind, Xian 710021, Shaanxi, Peoples R China

[3] Northwest Univ, Coll Chem & Mat Sci, Xian 710127, Shaanxi, Peoples R China

来源：

RSC ADVANCES | 2019年 / 9卷 / 59期

基金：

中国国家自然科学基金;

关键词：

SODIUM PERBORATE; BORONATE ESTERS; OXIDATION; MILD; GREEN; TRANSFORMATIONS; NANOPARTICLES; PERCARBONATE; ENERGIES; BENZENE;

D O I：

10.1039/c9ra07201b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalyst-free method for the hydroxylation of arylboronic acids to form the corresponding phenols with sodium perborate as the oxidant was developed using water as the solvent. Under the reaction conditions, the yield of phenol reached 92% at only 5 min. Moreover, the reaction could be conducted without a catalyst under the solvent-free condition, the efficiency of which was as high as that of a liquid-phase reaction. Using a microcalorimeter, the reaction was found to be an exothermic reaction. The reaction mechanism was investigated and understood via DFT calculations, which revealed that it was a nucleophilic reaction.

引用

页码：34529 / 34534

页数：6

共 50 条

[1] Biosilica as an efficient heterogeneous catalyst for ipso-hydroxylation of arylboronic acids
Mahanta, Abhijit
Adhikari, Pooja
Bora, Utpal
Thakur, Ashim Jyoti
TETRAHEDRON LETTERS, 2015, 56 (14) : 1780 - 1783
[2] Preparation of phenolic compounds through catalyst-free ipso-hydroxylation of arylboronic acids
Gohain, Mukut
du Plessis, Maretha
van Tonder, Johannes H.
Bezuidenhoudt, Barend C. B.
TETRAHEDRON LETTERS, 2014, 55 (13) : 2082 - 2084
[3] Arylazopyrazole linked Schiff bases as organocatalysts for the ipso-hydroxylation of arylboronic acids for the synthesis of phenols
Kumar, Manish
Degani, Mariam S.
TETRAHEDRON LETTERS, 2023, 131
[4] A mild and efficient protocol for the ipso-hydroxylation of arylboronic acids
Gogoi, Ankur
Bora, Utpal
TETRAHEDRON LETTERS, 2013, 54 (14) : 1821 - 1823
[5] Cellulose as recyclable organocatalyst for ipso-hydroxylation of arylboronic acids
Laskar, Khairujjaman
Paul, Subham
Bora, Utpal
TETRAHEDRON LETTERS, 2019, 60 (38)
[6] Tylenol® and Aspirin® as Green Promoters for Ipso-Hydroxylation of Arylboronic Acids
Kwon, Gyu-Tae
Kim, Seung-Hoi
LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (10) : 902 - 907
[7] A chemoselective ipso-hydroxylation of arylboronic acids using urea-hydrogen peroxide under catalyst free condition
Gupta, Surabhi
Chaudhary, Priyanka
Srivastava, Vandana
Kandasamy, Jeyakumar
TETRAHEDRON LETTERS, 2016, 57 (23) : 2506 - 2510
[8] Clay entrapped Cu(OH)x as an efficient heterogeneous catalyst for ipso-hydroxylation of arylboronic acids
Dar, Bashir Ahmad
Bhatti, Prince
Singh, A. P.
Lazar, Anish
Sharma, Parduman R.
Sharma, Meena
Singh, Baldev
APPLIED CATALYSIS A-GENERAL, 2013, 466 : 60 - 67
[9] ipso-hydroxylation of arylboronic acids to phenols using solid H2O2 complexes
Prakash, GKS
Chacko, S
Panja, C
Mathew, T
Olah, GA
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3317 - U3317
[10] Graphene Oxide as a Carbocatalyst for Sustainable ipso-Hydroxylation of Arylboronic Acids: A Simple and Straightforward Strategy To Access Phenols
Karthik, Murugan
Suresh, Palaniswamy
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (09): : 9028 - 9034

← 1 2 3 4 5 →