Novel Method for Efficient Aerobic Oxidation of Silyl Ethers to Carbonyl Compounds Catalyzed with...

2
2004 Oxidation O 0212 Novel Method for Efficient Aerobic Oxidation of Silyl Ethers to Carbonyl Com- pounds Catalyzed with N-Hydroxyphthalimide (NHPI) and Lipophilic Co(II) Complexes. — A mild and catalytic protocol for the title reaction of a relatively wide range of both TMS and TBS ethers is demonstrated. This is the first example of clean oxidative conversion of silyl ethers to the corresponding carbonyl compounds using molecular oxygen. The reaction times are reasonable, and yields are in most cases ex- cellent. Phenolic TBS ethers survived intact under the presented reaction conditions. — (KARIMI*, B.; RAJABI, J.; Org. Lett. 6 (2004) 17, 2841-2844; Dep. Chem., Inst. Adv. Stud. Basic Sci., Gava Zang, Zanjan, Iran; Eng.) — Steudel 49- 046

Transcript of Novel Method for Efficient Aerobic Oxidation of Silyl Ethers to Carbonyl Compounds Catalyzed with...

Page 1: Novel Method for Efficient Aerobic Oxidation of Silyl Ethers to Carbonyl Compounds Catalyzed with N-Hydroxyphthalimide (NHPI) and Lipophilic Co(II) Complexes.

2004

OxidationO 0212 Novel Method for Efficient Aerobic Oxidation of Silyl Ethers to Carbonyl Com-

pounds Catalyzed with N-Hydroxyphthalimide (NHPI) and Lipophilic Co(II) Complexes. — A mild and catalytic protocol for the title reaction of a relatively wide range of both TMS and TBS ethers is demonstrated. This is the first example of clean oxidative conversion of silyl ethers to the corresponding carbonyl compounds using molecular oxygen. The reaction times are reasonable, and yields are in most cases ex-cellent. Phenolic TBS ethers survived intact under the presented reaction conditions. — (KARIMI*, B.; RAJABI, J.; Org. Lett. 6 (2004) 17, 2841-2844; Dep. Chem., Inst. Adv. Stud. Basic Sci., Gava Zang, Zanjan, Iran; Eng.) — Steudel

49- 046

Page 2: Novel Method for Efficient Aerobic Oxidation of Silyl Ethers to Carbonyl Compounds Catalyzed with N-Hydroxyphthalimide (NHPI) and Lipophilic Co(II) Complexes.

2004


SILYL FLUORIDE: LAMB-DIP SPECTRA and EQUILIBRIUM STRUCTURE Cristina PUZZARINI and Gabriele CAZZOLI Dipartimento di Chimica “G. Ciamician”, Università di.

SILYL FLUORIDE: LAMB-DIP SPECTRA and EQUILIBRIUM STRUCTURE Cristina PUZZARINI and Gabriele CAZZOLI Dipartimento di Chimica “G. Ciamician”, Università di.

Brook Rearrangement - Chemistrychemistry.syr.edu/totah/che676/support/3e1/3.BrookRearrangement.pdf · •Brook Rearrangement makes silyl enol ethers •Useful reaction in tandem with

Brook Rearrangement - Chemistrychemistry.syr.edu/totah/che676/support/3e1/3.BrookRearrangement.pdf · •Brook Rearrangement makes silyl enol ethers •Useful reaction in tandem with

Lanthanide alkyl and silyl compounds: synthesis ...

Lanthanide alkyl and silyl compounds: synthesis ...

Silyl-protective groups influencing the reactivity and ... · Silyl groups such as TBDPS, TBDMS, TIPS or TMS are well-known and widely used alcohol protective groups in organic chem-istry.

Silyl-protective groups influencing the reactivity and ... · Silyl groups such as TBDPS, TBDMS, TIPS or TMS are well-known and widely used alcohol protective groups in organic chem-istry.

Procedure for manipulating / analysing Dynamic NMR (DNMR) data (example: DNMR data for the compound 1-Silyl-1-Silacyclohexane, C5H10SiHSiH (schsih3) By.

Procedure for manipulating / analysing Dynamic NMR (DNMR) data (example: DNMR data for the compound 1-Silyl-1-Silacyclohexane, C5H10SiHSiH (schsih3) By.

Oral Health Care Access & Barriers€¦ · Oral Health Care Access & Barriers Among Asian American, Native Hawaiian, and Pacific Islander-Serving Health Centers • N=137 AA&NHPI-Serving

Oral Health Care Access & Barriers€¦ · Oral Health Care Access & Barriers Among Asian American, Native Hawaiian, and Pacific Islander-Serving Health Centers • N=137 AA&NHPI-Serving

THE ALLYLIC AMINATION OF SILYL ENOL ETHERS USING N, N …

THE ALLYLIC AMINATION OF SILYL ENOL ETHERS USING N, N …

Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and

Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and

Enantioselective,SilylProtectionof, Dioldonohoe.chem.ox.ac.uk/resources/051113LitXuezheng.pdfBackground How to achieve enantioselective silyl protection？ • Modified guanidines

Enantioselective,SilylProtectionof, Dioldonohoe.chem.ox.ac.uk/resources/051113LitXuezheng.pdfBackground How to achieve enantioselective silyl protection？ • Modified guanidines

Silyl Ketone Chemistry. Preparation and Reactions of Silyl ...€¦ · J. Am. Chem. SOC. 1986, 108, 7791-7800 7791 pyrany1oxy)dodecanoic acid, 1.38 1 g (3.15 mmol) of GPC-CdCIz, 0.854

Silyl Ketone Chemistry. Preparation and Reactions of Silyl ...€¦ · J. Am. Chem. SOC. 1986, 108, 7791-7800 7791 pyrany1oxy)dodecanoic acid, 1.38 1 g (3.15 mmol) of GPC-CdCIz, 0.854

Synthesis of 2-Alkyl Chromane-4-ones Using Hydrogen Bond ......Silyl Ketene Acetals Silyl ketene acetals are attractive nucleophiles for reaction with benzopyryliuim triflates in the

Synthesis of 2-Alkyl Chromane-4-ones Using Hydrogen Bond ......Silyl Ketene Acetals Silyl ketene acetals are attractive nucleophiles for reaction with benzopyryliuim triflates in the

ENCORE: UTILIZING CRITICAL LITERACY STRATEGIES IN … · 2019-12-14 · AIAN = American Indian and Alaskan Native; NHPI = Native Hawaiian or Pacific Islander NOTE: Data reflects only

ENCORE: UTILIZING CRITICAL LITERACY STRATEGIES IN … · 2019-12-14 · AIAN = American Indian and Alaskan Native; NHPI = Native Hawaiian or Pacific Islander NOTE: Data reflects only

Important Synthetic Technique: protecting groups. Using Silyl ethers to Protect Alcohols Protecting groups are used to temporarily deactivate a functional.

Important Synthetic Technique: protecting groups. Using Silyl ethers to Protect Alcohols Protecting groups are used to temporarily deactivate a functional.

Advancing Justice A Community of ContrAsts A community of contrasts 1 Policy makers in california must understand Asian American and Native Hawaiian and Pacific Islander (NHPI) communities.

Advancing Justice A Community of ContrAsts A community of contrasts 1 Policy makers in california must understand Asian American and Native Hawaiian and Pacific Islander (NHPI) communities.

TRANSITION METAL MEDIATED, STEREOSELECTIVE HIGHER …Figure 13.1.3 Crystal Structures of Diene, 13.1.2c 85 Figure 13.1.4 Crystal Structure of Catechol Silyl Substituted Cycloadduct,

TRANSITION METAL MEDIATED, STEREOSELECTIVE HIGHER …Figure 13.1.3 Crystal Structures of Diene, 13.1.2c 85 Figure 13.1.4 Crystal Structure of Catechol Silyl Substituted Cycloadduct,

California Institute of Technology 4... · 2019. 5. 22. · Chapter 4 – Nickel-Catalyzed Asymmetric Reductive Cross-Coupling of N-Hydroxyphthalimide Esters and Alkenyl Bromides

California Institute of Technology 4... · 2019. 5. 22. · Chapter 4 – Nickel-Catalyzed Asymmetric Reductive Cross-Coupling of N-Hydroxyphthalimide Esters and Alkenyl Bromides

Silyl Radical Activation of Alkyl Halides in ...chemlabs.princeton.edu/macmillan/wp-content/... · Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique

Silyl Radical Activation of Alkyl Halides in ...chemlabs.princeton.edu/macmillan/wp-content/... · Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique

PEG -DAIL Enhanced Catalysis Activity: Oxidation 1000 · N-Hydroxyphthalimide (NHPI)-oxime (DMG) catalyst system had better performance in the PEG 1000 -based functional dicationic

PEG -DAIL Enhanced Catalysis Activity: Oxidation 1000 · N-Hydroxyphthalimide (NHPI)-oxime (DMG) catalyst system had better performance in the PEG 1000 -based functional dicationic

Reaction of the Si O (SnMe Building Block with Silyl ......Reaction of the Si8O20(SnMe3)8 Building Block with Silyl Chlorides: A New Synthetic Methodology for Preparing Nanostructured

Reaction of the Si O (SnMe Building Block with Silyl ......Reaction of the Si8O20(SnMe3)8 Building Block with Silyl Chlorides: A New Synthetic Methodology for Preparing Nanostructured

MECHANISTIC STUDIES OF THE SILYL-HECK REACTION

MECHANISTIC STUDIES OF THE SILYL-HECK REACTION