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Literature DB >> 22059470

Iridium-catalyzed allylic fluorination of trichloroacetimidates.

Joseph J Topczewski¹, Timothy J Tewson, Hien M Nguyen.

Abstract

A rapid allylic fluorination method utilizing trichloroacetimidates in conjunction with an iridium catalyst has been developed. The reaction is conducted at room temperature under ambient air and relies on Et(3)N·3HF reagent to provide branched allylic fluorides with complete regioselectivity. This high-yielding reaction can be conducted on a multigram scale and shows considerable functional group tolerance. The use of [(18)F]KF·Kryptofix allowed (18)F(-) incorporation in 10 min.

Entities: Chemical

Mesh：

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Year: 2011 PMID： 22059470 DOI： 10.1021/ja2087213

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

23 in total

1. "It's a (Kinetic) Trap!" - Selectively Differentiating Allylic Azide Isomers.

Authors: Joseph J Topczewski; Matthew R Porter
Journal: Synlett Date: 2018-07 Impact factor: 2.454

2. Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines.

Authors: Matthew R Porter; Rami M Shaker; Cristian Calcanas; Joseph J Topczewski
Journal: J Am Chem Soc Date: 2018-01-10 Impact factor: 15.419

Review 3. 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

4. Late-stage [¹⁸F]Fluorination: New Solutions to Old Problems.

Authors: Allen F Brooks; Joseph J Topczewski; Naoko Ichiishi; Melanie S Sanford; Peter J H Scott
Journal: Chem Sci Date: 2014-12-01 Impact factor: 9.825

5. Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives.

Authors: Sota Akiyama; Koji Kubota; Malte S Mikus; Paulo H S Paioti; Filippo Romiti; Qinghe Liu; Yuebiao Zhou; Amir H Hoveyda; Hajime Ito
Journal: Angew Chem Int Ed Engl Date: 2019-07-16 Impact factor: 15.336

6. Synthesis of [¹⁸F]-γ-fluoro-α,β,-unsaturated esters and ketones via vinylogous ¹⁸F-fluorination of α-diazoacetates with [¹⁸F]AgF.

Authors: Stephen Thompson; So Jeong Lee; Isaac M Jackson; Naoko Ichiishi; Allen F Brooks; Melanie S Sanford; Peter J H Scott
Journal: Synthesis (Stuttg) Date: 2019-12 Impact factor: 3.157

Iridium-catalyzed allylic fluorination of trichloroacetimidates.

1. "It's a (Kinetic) Trap!" - Selectively Differentiating Allylic Azide Isomers.

2. Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines.

Review 3. Chemistry for Positron Emission Tomography: Recent Advances in ¹¹ C-, ¹⁸ F-, ¹³ N-, and ¹⁵ O-Labeling Reactions.

4. Late-stage [¹⁸F]Fluorination: New Solutions to Old Problems.

5. Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives.

6. Synthesis of [¹⁸F]-γ-fluoro-α,β,-unsaturated esters and ketones via vinylogous ¹⁸F-fluorination of α-diazoacetates with [¹⁸F]AgF.

7. Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis.

8. Pd-catalyzed C-H fluorination with nucleophilic fluoride.

9. Nickel-mediated oxidative fluorination for PET with aqueous [18F] fluoride.

10. Direct Access to β-Fluorinated Aldehydes by Nitrite-Modified Wacker Oxidation.

Review 3. Chemistry for Positron Emission Tomography: Recent Advances in 11 C-, 18 F-, 13 N-, and 15 O-Labeling Reactions.

Review 3. Chemistry for Positron Emission Tomography: Recent Advances in ¹¹ C-, ¹⁸ F-, ¹³ N-, and ¹⁵ O-Labeling Reactions.