Al(2)O(3)-supported Cu-Catalyzed Electrophilic Substitution by PhSeBr in Organoboranes, Organosilanes, and Organostannanes. A protocol for the synthesis of unsymmetrical diaryl and alkyl aryl selenides.
Alumina-supported copper sulfate efficiently catalyzes electrophilic substitution in organoborane, organosilanes, and organostannanes by phenylselenium bromide providing a novel and efficient route to the synthesis of unsymmetrical diaryl and alkyl aryl selenides. A series of aryl, alkyl, and heteroaryl phenyl selenides were obtained in high yields. The catalyst is inexpensive, eco- and user-friendly, and recyclable. The mechanism involving Cu-assisted nucleophilic displacement of Br in PhSeBr by mild nucleophiles is described.
Bhadra
Sukalyan
S
Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata-700032, India.
Saha
Amit
A
Ranu
Brindaban C
BC
D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D009947:Organotin Compounds / Q000737:chemistry*; D018036:Selenium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D001880:Boranes; D017646:Organosilicon Compounds; D009947:Organotin Compounds; D018036:Selenium Compounds; D003300:Copper