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Cas Database

863988-32-3

863988-32-3

Identification

  • Product Name:2-(4-methylpyridin-2-yl)phenol

  • CAS Number: 863988-32-3

  • EINECS:

  • Molecular Weight:185.225

  • Molecular Formula: C12H11NO

  • HS Code:

  • Mol File:863988-32-3.mol

Synonyms:2-(4-methylpyridin-2-yl)phenol

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Relevant articles and documentsAll total 8 Articles be found

Visible Light Induced Rhodium(I)-Catalyzed C?H Borylation

Thongpaen, Jompol,Manguin, Romane,Dorcet, Vincent,Vives, Thomas,Duhayon, Carine,Mauduit, Marc,Baslé, Olivier

supporting information, p. 15244 - 15248 (2019/10/22)

An efficient visible light induced rhodium(I)-catalyzed regioselective borylation of aromatic C?H bonds is reported. The photocatalytic system is based on a single NHC?RhI complex capable of both harvesting visible light and enabling the bond breaking/forming at room temperature. The chelating nature of the NHC-carboxylate ligand was critical to ensure the stability of the RhI complex and to provide excellent photocatalytic activities. Experimental mechanistic studies evidenced a photooxidative ortho C?H bond addition upon irradiation with blue LEDs, leading to a cyclometalated RhIII-hydride intermediate.

Directed: Ortho C-H borylation catalyzed using Cp?Rh(iii)-NHC complexes

Thongpaen, Jompol,Schmid, Thibault E.,Toupet, Loic,Dorcet, Vincent,Mauduit, Marc,Baslé, Olivier

supporting information, p. 8202 - 8205 (2018/07/29)

Cp?Rh(NHC) complexes with bulky chiral bidentate NHC-carboxylate ligands were efficiently synthesized and fully characterized including solid-state structures. These unprecedented rhodium(iii) complexes demonstrated high selectivity in pyridine-directed ortho-C-H borylation of arenes under mild conditions.

Aerobic Direct C(sp2)-H Hydroxylation of 2-Arylpyridines by Palladium Catalysis Induced with Aldehyde Auto-Oxidation

Das, Prasenjit,Saha, Debajyoti,Saha, Dibyajyoti,Guin, Joyram

, p. 6050 - 6054 (2016/09/09)

Herein we present a Pd-catalyzed direct C-H hydroxylation of 2-arylpyridines using molecular oxygen (O2) as the sole oxidant. The key aspects of the method include: (a) the activation of molecular oxygen with a nontoxic and inexpensive aldehyde

Direct ortho-Hydroxylation of 2-Phenylpyridines using Palladium(II) Chloride and Hydrogen Peroxide

Yamaguchi, Tomoaki,Yamaguchi, Eiji,Tada, Norihiro,Itoh, Akichika

supporting information, p. 2017 - 2021 (2015/06/23)

Direct functionalization of the ubiquitous C-H bond is receiving much attention because complex structures can be formed from simple precursors. This paper reports a useful method for the direct hydroxylation of 2-phenylpyridines using palladium(II) chloride and aqueous hydrogen peroxide. In this method, hydrogen peroxide, which has high atom efficiency, is employed as the oxidant and phenol derivatives are generated via C-H activation.

Synthesis of Chemically and Configurationally Stable Monofluoro Acylboronates: Effect of Ligand Structure on their Formation, Properties, and Reactivities

Noda, Hidetoshi,Bode, Jeffrey W.

supporting information, p. 3958 - 3966 (2015/04/14)

The recent disclosures of two classes of acylborons, potassium acyltrifluoroborates (KATs) and N-methyliminodiacetyl (MIDA) acylboronates, demonstrated that certain acylboron species can be both remarkably stable and uniquely reactive. Here we report new classes of ligands for acylboronates that have a significant influence on the formation, properties, and reactivities of acylboronates. Our systematic investigations identified a class of neutral, monofluoroboronates that can be prepared in a one step, gram-scale fashion from readily accessible KATs. These monofluoroboronates are stable to air, moisture, and silica gel chromatography and can be easily handled without any special precautions. X-ray crystallography, NMR spectroscopy, and HPLC studies showed that they are tetravalent, configurationally stable B-chiral acylboronates. Significantly, the ligands on the boronate allow for fine-tuning of the properties and reactivity of acylboronates. In amide-forming ligation with hydroxylamines under aqueous conditions, a considerable difference in reactivity was observed as a function of ligand structure. The solid-state structures suggested that subtle steric and conformational factors modulate the reactivities of the acylboronates.

Process route upstream and downstream products

Process route

4-methyl-2-phenylpyridine
3475-21-6

4-methyl-2-phenylpyridine

2-(4-methylpyridin-2-yl)phenol
863988-32-3

2-(4-methylpyridin-2-yl)phenol

Conditions
Conditions Yield
With N-hydroxyphthalimide; oxygen; benzaldehyde; palladium dichloride; In toluene; at 100 ℃; for 15h; under 760.051 Torr; Schlenk technique;
75%
With dichloro bis(acetonitrile) palladium(II); oxygen; propionaldehyde; In 1,2-dichloro-ethane; at 100 ℃; under 760.051 Torr;
72%
With dihydrogen peroxide; palladium dichloride; In water; at 100 ℃; for 4h;
67%
Multi-step reaction with 2 steps
1.1: C28H38ClN2O2Rh; sodium methylate / benzene / 0.17 h / Glovebox; Schlenk technique; Inert atmosphere
1.2: 16 h / 80 °C / Schlenk technique; Sealed tube; Inert atmosphere
2.1: Oxone / water; acetone
With Oxone; C28H38ClN2O2Rh; sodium methylate; In water; acetone; benzene;
Multi-step reaction with 2 steps
1: C26H35N2O2Rh / tetrahydrofuran / 16 h / 25 °C / Inert atmosphere; Glovebox; Sealed tube; Irradiation
2: oxone||potassium monopersulfate triple salt / water; acetone / 2 h / Inert atmosphere; Glovebox
With oxone||potassium monopersulfate triple salt; C26H35N2O2Rh; In tetrahydrofuran; water; acetone;
4-methylpyridine-1-oxide
1003-67-4

4-methylpyridine-1-oxide

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

2-(4-methylpyridin-2-yl)phenol
863988-32-3

2-(4-methylpyridin-2-yl)phenol

Conditions
Conditions Yield
With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; at 28 ℃; for 3h; regioselective reaction; Inert atmosphere;
71%
4-methyl-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine

4-methyl-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine

2-(4-methylpyridin-2-yl)phenol
863988-32-3

2-(4-methylpyridin-2-yl)phenol

Conditions
Conditions Yield
With oxone||potassium monopersulfate triple salt; In water; acetone; for 2h; Inert atmosphere; Glovebox;
89%
With Oxone; In water; acetone;
2-(2-methoxyphenyl)-4-methylpyridine
100004-77-1

2-(2-methoxyphenyl)-4-methylpyridine

2-(4-methylpyridin-2-yl)phenol
863988-32-3

2-(4-methylpyridin-2-yl)phenol

Conditions
Conditions Yield
With pyridine hydrochloride; at 210 ℃;
76%
With pyridine hydrochloride; at 220 ℃;
2-Bromo-4-picoline
4926-28-7

2-Bromo-4-picoline

2-(4-methylpyridin-2-yl)phenol
863988-32-3

2-(4-methylpyridin-2-yl)phenol

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / tetrahydrofuran
2: pyridine hydrochloride / 210 °C
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); pyridine hydrochloride; In tetrahydrofuran;
Multi-step reaction with 3 steps
1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; toluene; ethanol / 12 h / 120 °C / Inert atmosphere; Schlenk technique
2.1: C28H38ClN2O2Rh; sodium methylate / benzene / 0.17 h / Glovebox; Schlenk technique; Inert atmosphere
2.2: 16 h / 80 °C / Schlenk technique; Sealed tube; Inert atmosphere
3.1: Oxone / water; acetone
With Oxone; tetrakis(triphenylphosphine) palladium(0); C28H38ClN2O2Rh; sodium methylate; sodium carbonate; In ethanol; water; acetone; toluene; benzene;
Multi-step reaction with 3 steps
1: 1-chloroisoquinoline; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 12 h / 120 °C / Inert atmosphere; Glovebox; Schlenk technique
2: C26H35N2O2Rh / tetrahydrofuran / 16 h / 25 °C / Inert atmosphere; Glovebox; Sealed tube; Irradiation
3: oxone||potassium monopersulfate triple salt / water; acetone / 2 h / Inert atmosphere; Glovebox
With tetrakis(triphenylphosphine) palladium(0); oxone||potassium monopersulfate triple salt; 1-chloroisoquinoline; C26H35N2O2Rh; sodium carbonate; In tetrahydrofuran; ethanol; water; acetone; toluene;
2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

2-(4-methylpyridin-2-yl)phenol
863988-32-3

2-(4-methylpyridin-2-yl)phenol

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: Pd(PPh3)4; aq. Na2CO3 / toluene; ethanol / Heating
2: pyridine hydrochloride / 220 °C
With tetrakis(triphenylphosphine) palladium(0); pyridine hydrochloride; sodium carbonate; In ethanol; toluene; 1: Suzuki coupling;
phenylboronic acid
98-80-6

phenylboronic acid

2-(4-methylpyridin-2-yl)phenol
863988-32-3

2-(4-methylpyridin-2-yl)phenol

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; toluene; ethanol / 12 h / 120 °C / Inert atmosphere; Schlenk technique
2.1: C28H38ClN2O2Rh; sodium methylate / benzene / 0.17 h / Glovebox; Schlenk technique; Inert atmosphere
2.2: 16 h / 80 °C / Schlenk technique; Sealed tube; Inert atmosphere
3.1: Oxone / water; acetone
With Oxone; tetrakis(triphenylphosphine) palladium(0); C28H38ClN2O2Rh; sodium methylate; sodium carbonate; In ethanol; water; acetone; toluene; benzene;
Multi-step reaction with 3 steps
1: 1-chloroisoquinoline; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 12 h / 120 °C / Inert atmosphere; Glovebox; Schlenk technique
2: C26H35N2O2Rh / tetrahydrofuran / 16 h / 25 °C / Inert atmosphere; Glovebox; Sealed tube; Irradiation
3: oxone||potassium monopersulfate triple salt / water; acetone / 2 h / Inert atmosphere; Glovebox
With tetrakis(triphenylphosphine) palladium(0); oxone||potassium monopersulfate triple salt; 1-chloroisoquinoline; C26H35N2O2Rh; sodium carbonate; In tetrahydrofuran; ethanol; water; acetone; toluene;
2-methoxyphenylmagnesium bromide
16750-63-3

2-methoxyphenylmagnesium bromide

2-(4-methylpyridin-2-yl)phenol
863988-32-3

2-(4-methylpyridin-2-yl)phenol

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / tetrahydrofuran
2: pyridine hydrochloride / 210 °C
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); pyridine hydrochloride; In tetrahydrofuran;
4-methyl-2-phenylpyridine
3475-21-6

4-methyl-2-phenylpyridine

2-(4-methylpyridin-2-yl)phenol
863988-32-3

2-(4-methylpyridin-2-yl)phenol

Conditions
Conditions Yield
With N-hydroxyphthalimide; oxygen; benzaldehyde; palladium dichloride; In toluene; at 100 ℃; for 15h; under 760.051 Torr; Schlenk technique;
75%
With dichloro bis(acetonitrile) palladium(II); oxygen; propionaldehyde; In 1,2-dichloro-ethane; at 100 ℃; under 760.051 Torr;
72%
With dihydrogen peroxide; palladium dichloride; In water; at 100 ℃; for 4h;
67%
Multi-step reaction with 2 steps
1.1: C28H38ClN2O2Rh; sodium methylate / benzene / 0.17 h / Glovebox; Schlenk technique; Inert atmosphere
1.2: 16 h / 80 °C / Schlenk technique; Sealed tube; Inert atmosphere
2.1: Oxone / water; acetone
With Oxone; C28H38ClN2O2Rh; sodium methylate; In water; acetone; benzene;
Multi-step reaction with 2 steps
1: C26H35N2O2Rh / tetrahydrofuran / 16 h / 25 °C / Inert atmosphere; Glovebox; Sealed tube; Irradiation
2: oxone||potassium monopersulfate triple salt / water; acetone / 2 h / Inert atmosphere; Glovebox
With oxone||potassium monopersulfate triple salt; C26H35N2O2Rh; In tetrahydrofuran; water; acetone;
4-methylpyridine-1-oxide
1003-67-4

4-methylpyridine-1-oxide

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

2-(4-methylpyridin-2-yl)phenol
863988-32-3

2-(4-methylpyridin-2-yl)phenol

Conditions
Conditions Yield
With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; at 28 ℃; for 3h; regioselective reaction; Inert atmosphere;
71%

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