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Literature DB >> 31573208

Dealkenylative Thiylation of C(sp³)-C(sp²) Bonds.

Abstract

Carbon-carbon bond fragmentations are useful methods for the functionalization of molecules. The value of such cleavage events is maximized when paired with subsequent bond formation. Herein we report a protocol for the cleavage of an alkene C(sp3)-C(sp2) bond, followed by the formation of a new C(sp3)-S bond. This reaction is performed in nonanhydrous solvent and open to the air, employs common starting materials, and can be used to rapidly diversify natural products.

Entities: Chemical Disease Gene Species

Year: 2019 PMID： 31573208 PMCID： PMC7337987 DOI： 10.1021/acs.orglett.9b03186

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

26 in total

Review 1. Radical-Promoted C-C Bond Cleavage: A Deconstructive Approach for Selective Functionalization.

Authors: Sara P Morcillo
Journal: Angew Chem Int Ed Engl Date: 2019-07-26 Impact factor: 15.336

2. Biomimetic synthesis of 5,6-dihydro-glaucogenin C: construction of the disecopregnane skeleton by iron(II)-promoted fragmentation of an α-alkoxy hydroperoxide.

Authors: Jinghan Gui; Dahai Wang; Weisheng Tian
Journal: Angew Chem Int Ed Engl Date: 2011-06-17 Impact factor: 15.336

3. Iron-catalyzed cross-coupling of unactivated secondary alkyl thio ethers and sulfones with aryl Grignard reagents.

Authors: Scott E Denmark; Alexander J Cresswell
Journal: J Org Chem Date: 2013-11-20 Impact factor: 4.354

Review 4. Thiols, thioethers, and related compounds as sources of C-centred radicals.

Authors: Fabrice Dénès; Carl H Schiesser; Philippe Renaud
Journal: Chem Soc Rev Date: 2013-07-05 Impact factor: 54.564

Review 5. Analysis of US FDA-Approved Drugs Containing Sulfur Atoms.

Authors: Kevin A Scott; Jon T Njardarson
Journal: Top Curr Chem (Cham) Date: 2018-01-22

6. Desulfonylative Arylation of Redox-Active Alkyl Sulfones with Aryl Bromides.

Authors: Jonathan M E Hughes; Patrick S Fier
Journal: Org Lett Date: 2019-07-05 Impact factor: 6.005

Review 7. Pharmacological properties of the ubiquitous natural product betulin.

Authors: Sami Alakurtti; Taru Mäkelä; Salme Koskimies; Jari Yli-Kauhaluoma
Journal: Eur J Pharm Sci Date: 2006-04-29 Impact factor: 4.384

Review 8. Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry.

Authors: Minghao Feng; Bingqing Tang; Steven H Liang; Xuefeng Jiang
Journal: Curr Top Med Chem Date: 2016 Impact factor: 3.295

9. Modular radical cross-coupling with sulfones enables access to sp³-rich (fluoro)alkylated scaffolds.

Authors: Rohan R Merchant; Jacob T Edwards; Tian Qin; Monika M Kruszyk; Cheng Bi; Guanda Che; Deng-Hui Bao; Wenhua Qiao; Lijie Sun; Michael R Collins; Olugbeminiyi O Fadeyi; Gary M Gallego; James J Mousseau; Philippe Nuhant; Phil S Baran
Journal: Science Date: 2018-02-18 Impact factor: 47.728

10. Structure-activity relationship study of betulinic acid, a novel and selective TGR5 agonist, and its synthetic derivatives: potential impact in diabetes.

Authors: Cédric Genet; Axelle Strehle; Céline Schmidt; Geoffrey Boudjelal; Annelise Lobstein; Kristina Schoonjans; Michel Souchet; Johan Auwerx; Régis Saladin; Alain Wagner
Journal: J Med Chem Date: 2010-01-14 Impact factor: 7.446

6 in total

1. Oxodealkenylative Cleavage of Alkene C(sp³ )-C(sp² ) Bonds: A Practical Method for Introducing Carbonyls into Chiral Pool Materials.

Authors: Andrew J Smaligo; Jason Wu; Nikolas R Burton; Allison S Hacker; Aslam C Shaikh; Jason C Quintana; Ruoxi Wang; Changmin Xie; Ohyun Kwon
Journal: Angew Chem Int Ed Engl Date: 2019-12-02 Impact factor: 15.336