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Literature DB >> 22308017

Cu(I)-catalyzed (11)C carboxylation of boronic acid esters: a rapid and convenient entry to (11)C-labeled carboxylic acids, esters, and amides.

Patrick J Riss¹, Shuiyu Lu, Sanjay Telu, Franklin I Aigbirhio, Victor W Pike.

Abstract

Rapid and direct: the carboxylation of boronic acid esters with (11)CO(2) provides [(11)C]carboxylic acids as a convenient entry into [(11)C]esters and [(11)C]amides. This conversion of boronates is tolerant to diverse functional groups (e.g., halo, nitro, or carbonyl).

Entities: Chemical

Mesh：

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Year: 2012 PMID： 22308017 PMCID： PMC3299884 DOI： 10.1002/anie.201107263

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

20 in total

Review 1. Synthesis of 11C, 18F, 15O, and 13N radiolabels for positron emission tomography.

Authors: Philip W Miller; Nicholas J Long; Ramon Vilar; Antony D Gee
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

2. Methods for the incorporation of carbon-11 to generate radiopharmaceuticals for PET imaging.

Authors: Peter J H Scott
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

3. Carboxylation of alkylboranes by N-heterocyclic carbene copper catalysts: synthesis of carboxylic acids from terminal alkenes and carbon dioxide.

Authors: Takeshi Ohishi; Liang Zhang; Masayoshi Nishiura; Zhaomin Hou
Journal: Angew Chem Int Ed Engl Date: 2011-07-07 Impact factor: 15.336

4. Synthesis of the enantiomers of [N-methyl-11C]PK 11195 and comparison of their behaviours as radioligands for PK binding sites in rats.

Authors: F Shah; S P Hume; V W Pike; S Ashworth; J McDermott
Journal: Nucl Med Biol Date: 1994-05 Impact factor: 2.408

5. Recent developments in carbon dioxide utilization under mild conditions.

Authors: Siti Nurhanna Riduan; Yugen Zhang
Journal: Dalton Trans Date: 2010-01-21 Impact factor: 4.390

6. Labeling proteins with fluorine-18 using N-succinimidyl 4-[18F]fluorobenzoate.

Authors: G Vaidyanathan; M R Zalutsky
Journal: Int J Rad Appl Instrum B Date: 1992-04

7. Beta-methyl[1-11C]heptadecanoic acid: a new myocardial metabolic tracer for positron emission tomography.

Authors: E Livni; D R Elmaleh; S Levy; G L Brownell; W H Strauss
Journal: J Nucl Med Date: 1982-02 Impact factor: 10.057

8. One-pot, direct incorporation of [11C]CO2 into carbamates.

Authors: Jacob M Hooker; Achim T Reibel; Sidney M Hill; Michael J Schueller; Joanna S Fowler
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

9. A comparative study of N.C.A. fluorine-18 labeling of proteins via acylation and photochemical conjugation.

Authors: H J Wester; K Hamacher; G Stöcklin
Journal: Nucl Med Biol Date: 1996-04 Impact factor: 2.408

10. Copper(I)-catalyzed carboxylation of aryl- and alkenylboronic esters.

Authors: Jun Takaya; Satoshi Tadami; Kazutoshi Ukai; Nobuharu Iwasawa
Journal: Org Lett Date: 2008-05-29 Impact factor: 6.005

21 in total

Review 1. Considerations in the Development of Reversibly Binding PET Radioligands for Brain Imaging.

Authors: Victor W Pike
Journal: Curr Med Chem Date: 2016 Impact factor: 4.530

Review 2. (11)C[double bond, length as m-dash]O bonds made easily for positron emission tomography radiopharmaceuticals.

Authors: Benjamin H Rotstein; Steven H Liang; Michael S Placzek; Jacob M Hooker; Antony D Gee; Frédéric Dollé; Alan A Wilson; Neil Vasdev
Journal: Chem Soc Rev Date: 2016-08-22 Impact factor: 54.564

3. New synthesis and tritium labeling of a selective ligand for studying high-affinity γ-hydroxybutyrate (GHB) binding sites.

Authors: Stine B Vogensen; Aleš Marek; Tina Bay; Petrine Wellendorph; Jan Kehler; Christoffer Bundgaard; Bente Frølund; Martin H F Pedersen; Rasmus P Clausen
Journal: J Med Chem Date: 2013-10-04 Impact factor: 7.446

4. Synthesis of [(11)C]Am80 via Novel Pd(0)-Mediated Rapid [(11)C]Carbonylation Using Arylboronate and [(11)C]Carbon Monoxide.

Authors: Misato Takashima-Hirano; Hideki Ishii; Masaaki Suzuki
Journal: ACS Med Chem Lett Date: 2012-08-16 Impact factor: 4.345

Review 5. Chemistry for Positron Emission Tomography: Recent Advances in ¹¹ C-, ¹⁸ F-, ¹³ N-, and ¹⁵ O-Labeling Reactions.

Authors: Xiaoyun Deng; Jian Rong; Lu Wang; Neil Vasdev; Lei Zhang; Lee Josephson; Steven H Liang
Journal: Angew Chem Int Ed Engl Date: 2019-01-14 Impact factor: 15.336

Cu(I)-catalyzed (11)C carboxylation of boronic acid esters: a rapid and convenient entry to (11)C-labeled carboxylic acids, esters, and amides.

Review 1. Synthesis of 11C, 18F, 15O, and 13N radiolabels for positron emission tomography.

2. Methods for the incorporation of carbon-11 to generate radiopharmaceuticals for PET imaging.

3. Carboxylation of alkylboranes by N-heterocyclic carbene copper catalysts: synthesis of carboxylic acids from terminal alkenes and carbon dioxide.

4. Synthesis of the enantiomers of [N-methyl-11C]PK 11195 and comparison of their behaviours as radioligands for PK binding sites in rats.

5. Recent developments in carbon dioxide utilization under mild conditions.

6. Labeling proteins with fluorine-18 using N-succinimidyl 4-[18F]fluorobenzoate.

7. Beta-methyl[1-11C]heptadecanoic acid: a new myocardial metabolic tracer for positron emission tomography.

8. One-pot, direct incorporation of [11C]CO2 into carbamates.

9. A comparative study of N.C.A. fluorine-18 labeling of proteins via acylation and photochemical conjugation.

10. Copper(I)-catalyzed carboxylation of aryl- and alkenylboronic esters.

Review 1. Considerations in the Development of Reversibly Binding PET Radioligands for Brain Imaging.

Review 2. (11)C[double bond, length as m-dash]O bonds made easily for positron emission tomography radiopharmaceuticals.

3. New synthesis and tritium labeling of a selective ligand for studying high-affinity γ-hydroxybutyrate (GHB) binding sites.

4. Synthesis of [(11)C]Am80 via Novel Pd(0)-Mediated Rapid [(11)C]Carbonylation Using Arylboronate and [(11)C]Carbon Monoxide.

Review 5. Chemistry for Positron Emission Tomography: Recent Advances in ¹¹ C-, ¹⁸ F-, ¹³ N-, and ¹⁵ O-Labeling Reactions.

6. [¹¹C]Cyanation of arylboronic acids in aqueous solutions.

7. "In-loop" [¹¹ C]CO₂ fixation: Prototype and proof of concept.

Review 8. 11CO2 fixation: a renaissance in PET radiochemistry.

9. Synthesis of [(11)C]Bexarotene by Cu-Mediated [(11)C]Carbon Dioxide Fixation and Preliminary PET Imaging.

10. Synthesis of Diverse (11)C-Labeled PET Radiotracers via Direct Incorporation of [(11)C]CO2.

Review 1. Synthesis of 11C, 18F, 15O, and 13N radiolabels for positron emission tomography.

Review 1. Considerations in the Development of Reversibly Binding PET Radioligands for Brain Imaging.

Review 2. (11)C[double bond, length as m-dash]O bonds made easily for positron emission tomography radiopharmaceuticals.

Review 5. Chemistry for Positron Emission Tomography: Recent Advances in 11 C-, 18 F-, 13 N-, and 15 O-Labeling Reactions.

Review 8. 11CO2 fixation: a renaissance in PET radiochemistry.

Review 5. Chemistry for Positron Emission Tomography: Recent Advances in ¹¹ C-, ¹⁸ F-, ¹³ N-, and ¹⁵ O-Labeling Reactions.