title: Multicomponent type II anion relay chemistry (ARC): one-pot syntheses of 2,3-disubstituted furans and thiophenes.
abstract: Effective, one-pot syntheses of 2,3-disubstituted furans and thiophenes, exploiting 2-tert-butyldimethylsilyl-3-formylfuran and -thiophene as the respective bifunctional linchpins, have been developed. The synthetic protocol involves multicomponent type II Anion Relay Chemistry (ARC) mediated by a solvent-controlled C(sp(2))-->O 1,4-Brook rearrangement. Simple organolithiums and alpha-disubstituted ester enolates prove effective as the initiating nucleophiles.
authors.affiliation: Department of Chemistry, Washington State University, Pullman, Washington 99164, USA.
authors.forename: Nelmi O
authors.initials: NO
authors.lastname: Devarie-Baez
authors.forename: Won-Suk
authors.initials: WS
authors.lastname: Kim
authors.forename: Amos B
authors.initials: AB
authors.lastname: Smith
authors.forename: Ming
authors.initials: M
authors.lastname: Xian
mesh_terms: D000838:Anions; D020650:Combinatorial Chemistry Techniques; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000838:Anions; D005663:Furans; D009942:Organometallic Compounds; D013876:Thiophenes; D008094:Lithium