Catalytic direct-type substitution reaction of α-alkylenolates: a Pd/Brønsted base-catalysed approach to the decarboxylative allylation of sulfonylimidates‡

Literature Information

Publication Date 2008-10-29
DOI 10.1039/B815845B
Impact Factor 6.222
Authors

S. B. Jennifer Kan, Ryosuke Matsubara, Florian Berthiol, Shū Kobayashi


View Original

Abstract

A mild and efficient process for the direct-type catalytic allylation of sulfonylimidates has been developed; this reaction represents the first example of Brønsted base-catalysed, in situ generation and use of α-alkylenolates in substitution reactions; the success of this methodology stems from the tunable α-proton acidity and nucleophilicity of sulfonylimidates, which could be harnessed in the realization of a broader range of catalytic direct-type reactions using ester equivalents as nucleophiles.

Related Literature

Oxygen-assisted reduction of Au species on Au/SiO2catalyst in room temperature CO oxidation

Zili Wu, Shenghu Zhou, Haoguo Zhu, Sheng Dai, Steven H. Overbury

2008-06-05 Communication

DOI: 10.1039/B803834A

Back cover

Front/Back Matter

DOI: 10.1039/B710035N

Csp3–F bond activation by nucleophilic attack of the {Pt2S2} core assisted by non-covalent interactions

Ainara Nova, Gregori Ujaque, Pilar González-Duarte, Agustí Lledós

2008-04-29 Communication

DOI: 10.1039/B801889H

Probing the stable G-quadruplex transition using quencher-free end-stacking ethynyl pyrene–adenosine

Young Jun Seo, Il Joon Lee, Jeong Wu Yi, Byeang Hyean Kim

2007-06-18 Communication

DOI: 10.1039/B707278C

Nickel-catalyzed cross-coupling reactions of benzylic zinc reagents with aromatic bromides, chlorides and tosylates

Matthias A. Schade, Albrecht Metzger, Stephan Hug, Paul Knochel

2008-04-24 Communication

DOI: 10.1039/B803072C

Simple linear asymmetrical complexes of silver(i): NC–Ag–NH3 and Br–Ag–NH3

Ann M. Chippindale, Laura E. Head, Simon J. Hibble

2008-05-14 Communication

DOI: 10.1039/B803500H

1,3-Diindolylureas: high affinity dihydrogen phosphate receptors

Claudia Caltagirone, Philip A. Gale, Jennifer R. Hiscock, Simon J. Brooks, Michael B. Hursthouse, Mark E. Light

2008-05-29 Communication

DOI: 10.1039/B806238B

Sulfonated N-heterocyclic carbenes for Suzuki coupling in water

Christoph Fleckenstein, Sutapa Roy, Steffen Leuthäußer, Herbert Plenio

2007-05-02 Communication

DOI: 10.1039/B703658B

Asymmetric multifunctional organocatalytic Michael addition of nitroalkanes to α,β-unsaturated ketones

Pengfei Li, Yongcan Wang, Jinxing Ye

2008-05-16 Communication

DOI: 10.1039/B804540B

You might also like

Compound Q&A

Are there alternatives to 1-(4-Chlorophenyl)-N-hydroxymethanimine (CAS: 3848-36-0) in synthesis?

When considering alternatives to 1-(4-Chlorophenyl)-N-hydroxymethanimine (CAS: 3...

3848-36-01-(4-Chlorophenyl)-N...
Compound Q&A

How is 3-(4-Bromophenyl)-5-(2-fluorophenyl)-1,2,4-oxadiazole (CAS: 419553-16-5) typically synthesized?

3-(4-Bromophenyl)-5-(2-fluorophenyl)-1,2,4-oxadiazole is synthesized through a m...

419553-16-53-(4-Bromophenyl)-5-...
Compound Q&A

How is 5-Chloro-2-(4-chlorophenyl)-4-methyl-6-[3-(1-piperidinyl)propoxy]pyrimidine (CAS: 1639220-19-1) typically synthesized?

5-Chloro-2-(4-chlorophenyl)-4-methyl-6-[3-(1-piperidinyl)propoxy]pyrimidine (CAS...

1639220-19-15-Chloro-2-(4-chloro...
Compound Q&A

What industries use 2-Chloro-4-(difluoromethoxy)pyridine (CAS: 1206978-15-5)?

2-Chloro-4-(difluoromethoxy)pyridine is used in the pharmaceutical industry for ...

1206978-15-52-Chloro-4-(difluoro...
Compound Q&A

What regulatory guidelines apply to 3-Chloro-6-methylpyridazine (CAS: 1121-79-5)?

3-Chloro-6-methylpyridazine (CAS: 1121-79-5) is classified under the Globally Ha...

1121-79-53-Chloro-6-methylpyr...
Compound Q&A

Are there alternatives to Methyl 4,5-dimethyl-2-nitrobenzoate in synthesis?

Several alternatives can be used in the synthesis of Methyl 4,5-dimethyl-2-nitro...

90922-74-0Methyl 4,5-dimethyl-...
Compound Q&A

Are there alternatives to (2E,2'E)-3,3'-(1,4-Phenylene)bisacrylaldehyde in synthesis?

Alternatives to (2E,2'E)-3,3'-(1,4-Phenylene)bisacrylaldehyde include other acry...

63405-68-5(2E,2'E)-3,3'-(1,4-P...
Compound Q&A

What is 3-Amino-5-chloropyridin-2-ol hydrochloride (CAS: 1261906-29-9)?

3-Amino-5-chloropyridin-2-ol hydrochloride is an organic compound with the CAS n...

1261906-29-93-Amino-5-chloropyri...
Compound Q&A

What precautions should be taken when handling 6,7-Difluoro-2,3-dihydro-4H-chromen-4-one (CAS: 1092349-93-3)?

When handling 6,7-Difluoro-2,3-dihydro-4H-chromen-4-one, it is essential to wear...

1092349-93-36,7-Difluoro-2,3-dih...

Source Journal

Chemical Communications

Chemical Communications
CiteScore: 8.6
Self-citation Rate: 4.7%
Articles per Year: 2458

ChemComm publishes urgent research which is of outstanding significance and interest to experts in the field, while also appealing to the journal’s broad chemistry readership. Our communication format is ideally suited to short, urgent studies that are of such importance that they require accelerated publication. Our scope covers all topics in chemistry, and research at the interface of chemistry and other disciplines (such as materials science, nanoscience, physics, engineering and biology) where there is a significant novelty in the chemistry aspects. Major topic areas covered include: Analytical Chemistry Catalysis Chemical Biology and medicinal chemistry Computational Chemistry and Machine Learning Energy and sustainable chemistry Environmental Chemistry Green Chemistry Inorganic Chemistry Materials Chemistry Nanoscience Organic Chemistry Physical Chemistry Polymer Chemistry Supramolecular Chemistry

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.