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Literature DB >> 28762258

HBr-DMPU: The First Aprotic Organic Solution of Hydrogen Bromide.

Zhou Li¹, Rene Ebule¹, Jessica Kostyo¹, Gerald B Hammond¹, Bo Xu².

Abstract

HBr and DMPU (1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone) form a room-temperature-stable complex that provides a mild, effective, and selective hydrobrominating reagent toward alkynes, alkenes, and allenes. HBr-DMPU could also replace other halogenating reagents in the halo-Prins reaction, ether cleavage, and deoxy-bromination reactions.

Entities: Chemical Gene

Keywords: bromide; halides; hydrogen; hydrohalogenation; organic halide

Year: 2017 PMID： 28762258 PMCID： PMC5682921 DOI： 10.1002/chem.201703457

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

30 in total

1. A ring expansion-annulation strategy for the synthesis of substituted azulenes. Preparation and Suzuki coupling reactions of 1-azulenyl triflates.

Authors: J L Kane; K M Shea; A L Crombie; R L Danheiser
Journal: Org Lett Date: 2001-04-05 Impact factor: 6.005

2. Why Are Vinyl Cations Sluggish Electrophiles?

Authors: Peter A Byrne; Shinjiro Kobayashi; Ernst-Ulrich Würthwein; Johannes Ammer; Herbert Mayr
Journal: J Am Chem Soc Date: 2017-01-20 Impact factor: 15.419

Review 3. Large-scale applications of transition metal-catalyzed couplings for the synthesis of pharmaceuticals.

Authors: Javier Magano; Joshua R Dunetz
Journal: Chem Rev Date: 2011-03-09 Impact factor: 60.622

Review 4. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors: Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal: Chem Rev Date: 2013-03-19 Impact factor: 60.622

5. 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

6. The concerted addition of HBr to aryl alkynes; orthogonal pi bond selectivity.

Authors: Hilton M Weiss; Kim M Touchette; Sarah Angell; Jihan Khan
Journal: Org Biomol Chem Date: 2003-06-21 Impact factor: 3.876

7. Regiochemical variation in the electrophilic addition of HBr to 1-phenylprop-1-yne.

Authors: Hilton M Weiss; Kim M Touchette; Frantz Andersen; David Iskhakov
Journal: Org Biomol Chem Date: 2003-06-21 Impact factor: 3.876

8. Olefin metathesis reactions with vinyl halides: formation, observation, interception, and fate of the ruthenium-monohalomethylidene moiety.

Authors: Marisa L Macnaughtan; Marc J A Johnson; Jeff W Kampf
Journal: J Am Chem Soc Date: 2007-06-02 Impact factor: 15.419

9. 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

HBr-DMPU: The First Aprotic Organic Solution of Hydrogen Bromide.

1. A ring expansion-annulation strategy for the synthesis of substituted azulenes. Preparation and Suzuki coupling reactions of 1-azulenyl triflates.

2. Why Are Vinyl Cations Sluggish Electrophiles?

Review 3. Large-scale applications of transition metal-catalyzed couplings for the synthesis of pharmaceuticals.

Review 4. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

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

6. The concerted addition of HBr to aryl alkynes; orthogonal pi bond selectivity.

7. Regiochemical variation in the electrophilic addition of HBr to 1-phenylprop-1-yne.

8. Olefin metathesis reactions with vinyl halides: formation, observation, interception, and fate of the ruthenium-monohalomethylidene moiety.

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

10. Direct synthesis of Z-alkenyl halides through catalytic cross-metathesis.

1. Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2.

2. Metal-free Chlorothiolation of Alkenes using HCl and Sulfoxides.

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

4. Metal-free, Regio-, and Stereo-Controlled Hydrochlorination and Hydrobromination of Ynones and Ynamides.

5. Iridium-Catalyzed Hydrochlorination and Hydrobromination of Alkynes by Shuttle Catalysis.