Multicomponent type II anion relay chemistry (ARC): one-pot syntheses of 2,3-disubstituted furans and thiophenes

Nelmi O Devarie-Baez; Won-Suk Kim; Amos B Smith; Ming Xian

doi:10.1021/ol900434k

Multicomponent type II anion relay chemistry (ARC): one-pot syntheses of 2,3-disubstituted furans and thiophenes

Org Lett. 2009 Apr 16;11(8):1861-4. doi: 10.1021/ol900434k.

Authors

Nelmi O Devarie-Baez¹, Won-Suk Kim, Amos B Smith, Ming Xian

Affiliation

¹ Department of Chemistry, Washington State University, Pullman, Washington 99164, USA.

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.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Anions
Combinatorial Chemistry Techniques
Furans / chemical synthesis*
Furans / chemistry
Lithium / chemistry
Molecular Structure
Organometallic Compounds / chemistry
Thiophenes / chemical synthesis*
Thiophenes / chemistry

Substances

Anions
Furans
Organometallic Compounds
Thiophenes
Lithium

Abstract

Publication types

MeSH terms

Substances

Grants and funding