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Literature DB >> 26167268

Formal Asymmetric Hydrobromination of Styrenes via Copper-Catalyzed 1,3-Halogen Migration.

R J Van Hoveln¹, S C Schmid¹, M Tretbar¹, C T Buttke¹, J M Schomaker¹.

Abstract

An enantioselective Cu(I)-catalyzed 1,3-halogen migration reaction accomplishes a formal hydrobromination by transferring a bromine activating group from a sp2 carbon to a benzylic carbon in good er and with concomitant borylation of the Ar-Br bond. Computational modelling aids in understanding the reaction outcome and suggests future directions to improve the formal asymmetric hydrobromination. The benzyl bromide can be displaced with a variety of nucleophiles to produce a wide array of functionalized products.

Entities: Chemical Gene Species

Year: 2014 PMID： 26167268 PMCID： PMC4494760 DOI： 10.1039/C4SC02040E

Source DB: PubMed Journal: Chem Sci ISSN： 2041-6520 Impact factor: 9.825

35 in total

Review 1. New catalytic approaches towards the enantioselective halogenation of alkenes.

Authors: Ulrich Hennecke
Journal: Chem Asian J Date: 2012-02-07

2. Ionic liquid media resulted in the first asymmetric aminohalogenation reaction of alkenes.

Authors: Xin Xu; S R S Saibabu Kotti; Junying Liu; John F Cannon; Allan D Headley; Guigen Li
Journal: Org Lett Date: 2004-12-23 Impact factor: 6.005

3. Strategies for catalytic asymmetric electrophilic alpha halogenation of carbonyl compounds.

Authors: Martin Oestreich
Journal: Angew Chem Int Ed Engl Date: 2005-04-15 Impact factor: 15.336

4. Chiral calcium VAPOL phosphate mediated asymmetric chlorination and Michael reactions of 3-substituted oxindoles.

Authors: Wenhua Zheng; Zuhui Zhang; Matthew J Kaplan; Jon C Antilla
Journal: J Am Chem Soc Date: 2011-02-22 Impact factor: 15.419

5. Aryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: arene functionalization with activating group recycling.

Authors: Joel F Hooper; Adrian B Chaplin; Carlos González-Rodríguez; Amber L Thompson; Andrew S Weller; Michael C Willis
Journal: J Am Chem Soc Date: 2012-02-07 Impact factor: 15.419

2. Regio- and Stereospecific 1,3-Allyl Group Transfer Triggered by a Copper-Catalyzed Borylation/ortho-Cyanation Cascade.

Authors: Yang Yang
Journal: Angew Chem Int Ed Engl Date: 2015-10-28 Impact factor: 15.336

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

Authors: Peng Yu; Alessandro Bismuto; Bill Morandi
Journal: Angew Chem Int Ed Engl Date: 2020-01-16 Impact factor: 15.336

3 in total

Formal Asymmetric Hydrobromination of Styrenes via Copper-Catalyzed 1,3-Halogen Migration.

Review 1. New catalytic approaches towards the enantioselective halogenation of alkenes.

2. Ionic liquid media resulted in the first asymmetric aminohalogenation reaction of alkenes.

3. Strategies for catalytic asymmetric electrophilic alpha halogenation of carbonyl compounds.

4. Chiral calcium VAPOL phosphate mediated asymmetric chlorination and Michael reactions of 3-substituted oxindoles.

5. Aryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: arene functionalization with activating group recycling.

6. Iodine recycling via 1,3-migration in iodoindoles under metal catalysis.

Review 7. Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective.

8. New palladium(II)-catalyzed asymmetric 1,2-dibromo synthesis.

9. Enantioselective bromolactonization of conjugated (Z)-enynes.

10. Enantioselective dichlorination of allylic alcohols.

1. Mechanistic studies of copper(I)-catalyzed 1,3-halogen migration.

2. Regio- and Stereospecific 1,3-Allyl Group Transfer Triggered by a Copper-Catalyzed Borylation/ortho-Cyanation Cascade.

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