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Literature DB >> 26331916

Manganese-Catalyzed Oxidative Azidation of Cyclobutanols: Regiospecific Synthesis of Alkyl Azides by C-C Bond Cleavage.

Rongguo Ren¹, Huijun Zhao¹, Leitao Huan¹, Chen Zhu^2,3.

Abstract

A novel, manganese-catalyzed oxidative azidation of cyclobutanols is described. A wide range of primary, secondary, and tertiary alkyl azides were generated in synthetically useful yields and exclusive regioselectivity. Aside from linear alkyl azides, otherwise elusive medium-sized cyclic azides were also readily prepared. Preliminary mechanistic studies reveal that the reaction likely proceeds by a radical-mediated C-C bond cleavage/C-N3 bond formation pathway.

Entities: Chemical

Keywords: CC cleavage; azidation; azides; cyclobutanols; manganese

Year: 2015 PMID： 26331916 DOI： 10.1002/anie.201506578

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

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Cited

15 in total

1. A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C-C Bond Cleavage Reactions.

Authors: Eisuke Ota; Huaiju Wang; Nils Lennart Frye; Robert R Knowles
Journal: J Am Chem Soc Date: 2019-01-15 Impact factor: 15.419

2. Regio- and Stereoselective Rhodium(II)-Catalyzed C-H Functionalization of Cyclobutanes.

Authors: Zachary J Garlets; Benjamin D Wertz; Wenbin Liu; Eric A Voight; Huw M L Davies
Journal: Chem Date: 2020-01-09 Impact factor: 22.804

3. Late Stage Azidation of Complex Molecules.

Authors: Rashad R Karimov; Ankit Sharma; John F Hartwig
Journal: ACS Cent Sci Date: 2016-10-07 Impact factor: 14.553

4. Rhodium(i)-catalyzed asymmetric [4 + 2] cycloaddition reactions of 2-alkylenecyclobutanols with cyclic enones through C-C bond cleavage: efficient access to trans-bicyclic compounds.

Authors: Xinxin Zheng; Rui Guo; Guozhu Zhang; Dayong Zhang
Journal: Chem Sci Date: 2018-01-08 Impact factor: 9.825

Review 5. Metal-Catalysed Azidation of Organic Molecules.

Authors: Monalisa Goswami; Bas de Bruin
Journal: European J Org Chem Date: 2016-12-22

6. Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp³)-C(sp³) bond cleavage.

Authors: Rui Guo; Xinxin Zheng; Dayong Zhang; Guozhu Zhang
Journal: Chem Sci Date: 2017-01-23 Impact factor: 9.825

Manganese-Catalyzed Oxidative Azidation of Cyclobutanols: Regiospecific Synthesis of Alkyl Azides by C-C Bond Cleavage.

1. A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C-C Bond Cleavage Reactions.

2. Regio- and Stereoselective Rhodium(II)-Catalyzed C-H Functionalization of Cyclobutanes.

3. Late Stage Azidation of Complex Molecules.

4. Rhodium(i)-catalyzed asymmetric [4 + 2] cycloaddition reactions of 2-alkylenecyclobutanols with cyclic enones through C-C bond cleavage: efficient access to trans-bicyclic compounds.

Review 5. Metal-Catalysed Azidation of Organic Molecules.

6. Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp³)-C(sp³) bond cleavage.

7. Silver-catalyzed remote Csp³-H functionalization of aliphatic alcohols.

8. Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp³)-H bonds.

9. Visible-light-driven palladium-catalyzed Dowd-Beckwith ring expansion/C-C bond formation cascade.

10. Photoinduced Remote Functionalisations by Iminyl Radical Promoted C-C and C-H Bond Cleavage Cascades.