Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Metal-free Regioselective Hydrochlorination of Unactivated Alkenes via a Combined Acid Catalytic System.

Literature DB >> 29750081

Metal-free Regioselective Hydrochlorination of Unactivated Alkenes via a Combined Acid Catalytic System.

Shengzong Liang¹, Gerald B Hammond¹, Bo Xu².

Abstract

A combined acid HCl/DMPU-acetic acid catalytic system was used in the hydrochlorination of a wide range of unactivated alkenes. This hydrochlorination strategy is remarkably greener than previous reported methods in terms of high atom efficiency, no toxic waste generated and metal-free process. The higher efficiency, compared with other commercially available HCl reagents, was augmented by the good regioselectivity and functionality tolerance found. A stepwise mechanism for this hydrochlorination process was proposed based on kinetic studies.

Entities: Chemical Disease

Year: 2018 PMID： 29750081 PMCID： PMC5937714 DOI： 10.1039/C7GC03665E

Source DB: PubMed Journal: Green Chem ISSN： 1463-9262 Impact factor: 10.182

30 in total

1. "Designer acids": combined acid catalysis for asymmetric synthesis.

Authors: Hisashi Yamamoto; Kentaro Futatsugi
Journal: Angew Chem Int Ed Engl Date: 2005-03-18 Impact factor: 15.336

2. Application of a robustness screen for the evaluation of synthetic organic methodology.

Authors: Karl D Collins; Andreas Rühling; Frank Glorius
Journal: Nat Protoc Date: 2014-05-15 Impact factor: 13.491

3. Scalable anti-Markovnikov hydrobromination of aliphatic and aromatic olefins.

Authors: Marzia Galli; Catherine J Fletcher; Marc Del Pozo; Stephen M Goldup
Journal: Org Biomol Chem Date: 2016-05-17 Impact factor: 3.876

4. Bromofluorination of Unsaturated Compounds using DMPU/HF as a Fluorinating Reagent.

Authors: Shengzong Liang; Francis J Barrios; Otome E Okoromoba; Zofia Hetman; Bo Xu; Gerald B Hammond
Journal: J Fluor Chem Date: 2017-08-04 Impact factor: 2.050

5. Multiple isotope effect study of the acid-catalyzed hydrolysis of formamide.

Authors: John F Marlier; Erica Campbell; Catherine Lai; Michael Weber; Laurie A Reinhardt; W W Cleland
Journal: J Org Chem Date: 2006-05-12 Impact factor: 4.354

6. Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions.

Authors: Otome E Okoromoba; Zhou Li; Nicole Robertson; Mark S Mashuta; Uenifer R Couto; Cláudio F Tormena; Bo Xu; Gerald B Hammond
Journal: Chem Commun (Camb) Date: 2016-11-08 Impact factor: 6.222

7. Designer HF-based fluorination reagent: highly regioselective synthesis of fluoroalkenes and gem-difluoromethylene compounds from alkynes.

Authors: Otome E Okoromoba; Junbin Han; Gerald B Hammond; Bo Xu
Journal: J Am Chem Soc Date: 2014-10-02 Impact factor: 15.419

2. Decarbonylative Transfer Hydrochlorination of Alkenes and Alkynes Based on a B(C₆ F₅ )₃ -Initiated Grob Fragmentation.

Authors: Kaixue Xie; Martin Oestreich
Journal: Angew Chem Int Ed Engl Date: 2022-04-11 Impact factor: 16.823

2 in total

Metal-free Regioselective Hydrochlorination of Unactivated Alkenes via a Combined Acid Catalytic System.

1. "Designer acids": combined acid catalysis for asymmetric synthesis.

2. Application of a robustness screen for the evaluation of synthetic organic methodology.

3. Scalable anti-Markovnikov hydrobromination of aliphatic and aromatic olefins.

4. Bromofluorination of Unsaturated Compounds using DMPU/HF as a Fluorinating Reagent.

5. Multiple isotope effect study of the acid-catalyzed hydrolysis of formamide.

6. Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions.

7. Designer HF-based fluorination reagent: highly regioselective synthesis of fluoroalkenes and gem-difluoromethylene compounds from alkynes.

8. A visible-light-promoted radical reaction system for azidation and halogenation of tertiary aliphatic C-H bonds.

9. Catalytic allylic oxidation of internal alkenes to a multifunctional chiral building block.

10. Chloride-Tolerant Gold(I)-Catalyzed Regioselective Hydrochlorination of Alkynes.

1. Synthesis of Alkyl Halides from Aldehydes via Deformylative Halogenation.

2. Decarbonylative Transfer Hydrochlorination of Alkenes and Alkynes Based on a B(C₆ F₅ )₃ -Initiated Grob Fragmentation.