Halogen‐Induced Friedel‐Crafts Alkenylation Reactions with Haloalkynes: Direct Access to gem‐1, 1‐Dihaloalkenes. Issue 32 (13th November 2017)

• Record Type: Journal Article
• Authors: Maji, Biswajit; Bhattacharya, Aditya; Hazra, Sunit
• Is Part Of: ChemistrySelect. Volume 2:Issue 32(2017)
• Page Start: 10375
• Page End: 10378
• Publication Date: 2017-11-13
• Subjects: Annulated arene carbocycle -- 1, 1-diarylalkene -- Friedel-Crafts alkenylation -- gem-dihaloalkene -- haloalkyne; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201702265
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A simple and efficient tactic for the synthesis of gem ‐hetero‐ or homo‐dihaloalkenes is reported from haloalkynes where Friedel‐Crafts alkenylation is a key step. The method provides functionalized tetrasubstituted alkenes which are important precursors in organic synthesis. The strategy is further extended with intramolecular Friedel‐Crafts alkenylation on ω ‐aryl alkynes to produce annulated arene carbocycles in a simple manner. Abstract : ICl‐induced an efficient inter‐ and intramolecular Friedel‐Crafts alkenylation reaction is developed under mild reaction condition. Intermolecular mode of arene addition to predefined haloalkynes provided gem ‐hetero‐ or homo‐dihaloalkenes in moderate to good yields and with good to excellent regio‐ and stereoselectivities. Intramolecular ω ‐aryl alkynes lead to annulated carbocycles in excellent yields.