Trichloroacetonitrile as an efficient activating agent for the ipso-hydroxylation of arylboronic acids to phenolic compounds

被引：14

作者：

Fang, Yuanding ^{[2
,3
]}

Zhao, Rong ^{[2
,3
]}

Yao, Yuan ^{[3
]}

Liu, Yang ^{[3
]}

Chang, Denghu ^{[2
,3
]}

Yao, Ming ^{[1
]}

Shi, Lei ^{[1
,2
,3
,4
]}

机构：

[1] Jingchu Univ Technol, Hubei Key Lab Drug Synth & Optimizat, Jingmen 448000, Peoples R China

[2] Harbin Inst Technol, Sch Sci, Shenzhen 518055, Peoples R China

[3] Harbin Inst Technol, Sch Chem & Chem Engn, MIIT Key Lab Crit Mat Technol New Energy Convers, Harbin 150001, Heilongjiang, Peoples R China

[4] Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 32期

基金：

中国国家自然科学基金;

关键词：

AEROBIC OXIDATIVE HYDROXYLATION; DEEP EUTECTIC MIXTURE; VISIBLE-LIGHT; HYDROGEN-PEROXIDE; BORONIC ACIDS; PHOTOREDOX CATALYSIS; ORGANIC FRAMEWORK; METAL; FACILE; MILD;

D O I：

10.1039/c9ob01568j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal-free and base-free Cl3CCN mediated method was developed for the ipso-hydroxylation of aryl boronic acids to their corresponding phenols, which was promoted by a key unstable Lewis adduct intermediate. This transformation has broad functional group tolerance, and late-stage functionalization was successful as well. After simple investigation, two pathways (radical/ionic mechanism) were suggested, and the beneficial action of blue light needs to be further studied.

引用

页码：7558 / 7563

页数：6

共 73 条

[1] Studies of the boron-carbon linkage Part I The oxidation and nitration of phenylboric acid [J].

Ainley, AD ;

Challenger, F .

JOURNAL OF THE CHEMICAL SOCIETY, 1930, :2171-2180

[2]

[Anonymous], 2009, Gaussian 09,Revision C.01

[3] EPOXIDATION OF ALKENES WITH TRICHLOROACETONITRILE HYDROGEN-PEROXIDE IN A NEUTRAL BIPHASIC SOLVENT SYSTEM [J].

ARIAS, LA ;

ADKINS, S ;

NAGEL, CJ ;

BACH, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (06) :888-890

[4] Transition-Metal-Catalyzed Allylic Substitutions of Trichloroacetimidates [J].

Arnold, Jeffrey S. ;

Zhang, Qi ;

Nguyen, Hien M. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (23) :4925-4948

[5] Catalysis by mont K-10 supported silver nanoparticles: a rapid and green protocol for the efficient ipso-hydroxylation of arylboronic acids [J].

Begum, Tahshina ;

Gogoi, Ankur ;

Gogoi, Pradip K. ;

Bora, Utpal .

TETRAHEDRON LETTERS, 2015, 56 (01) :95-97

[6] IPSO-Hydroxylation of Boronic Acid via Ozonolysis: A Metal-, Ligand-, and Base-free Method [J].

Bommegowda, Yadaganahalli K. ;

Mallesha, Ningegowda ;

Vinayaka, Ajjampura C. ;

Sadashiva, Maralinganadoddi P. .

CHEMISTRY LETTERS, 2016, 45 (03) :268-270

[7] Boron reagents in process chemistry: Excellent tools for selective reductions [J].

Burkhardt, Elizabeth R. ;

Matos, Karl .

CHEMICAL REVIEWS, 2006, 106 (07) :2617-2650

[8] Unexpected Phenol Production from Arylboronic Acids under Palladium-Free Conditions; Organocatalyzed Air Oxidation [J].

Cammidge, Andrew N. ;

Goddard, Victoria H. M. ;

Schubert, Christopher P. J. ;

Gopee, Hemant ;

Hughes, David L. ;

Gonzalez-Lucas, Daniel .

ORGANIC LETTERS, 2011, 13 (22) :6034-6037

[9] Boronic Acids and Esters in the Petasis-Borono Mannich Multicomponent Reaction [J].

Candeias, Nuno R. ;

Montalbano, Francesco ;

Cal, Pedro M. S. D. ;

Gois, Pedro M. P. .

CHEMICAL REVIEWS, 2010, 110 (10) :6169-6193

[10] A Green Alternative for the Conversion of Arylboronic Acids/Esters into Phenols Promoted by a Reducing Agent, Sodium Sulfite [J].

Castro-Godoy, Willber D. ;

Schmidt, Luciana C. ;

Arguello, Juan E. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (19) :3035-3039

← 1 2 3 4 5 6 7 8 →