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

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

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

33 Scopus citations

Abstract

Effective, one-pot syntheses of 2,3-disubstituted furans and thiophenes, exploiting 2-fert-butyldimethylsilyl-3-formylfuran and -thiophene as the respective Afunctional linchpins, have been developed. The synthetic protocol involves multicomponent type II Anion Relay Chemistry (ARC) mediated by a solvent-controlled C(sp ²)→0 1,4-Brook rearrangement. Simple organolithiums and α-disubstituted ester enolates prove effective as the initiating nucleophiles.

Original language	English
Pages (from-to)	1861-1864
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	8
DOIs	https://doi.org/10.1021/ol900434k
State	Published - 16 Apr 2009

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abstract = "Effective, one-pot syntheses of 2,3-disubstituted furans and thiophenes, exploiting 2-fert-butyldimethylsilyl-3-formylfuran and -thiophene as the respective Afunctional linchpins, have been developed. The synthetic protocol involves multicomponent type II Anion Relay Chemistry (ARC) mediated by a solvent-controlled C(sp 2)→0 1,4-Brook rearrangement. Simple organolithiums and α-disubstituted ester enolates prove effective as the initiating nucleophiles.",

author = "Devarie-Baez, \{Nelmi O.\} and Kim, \{Won Suk\} and Smith, \{Amos B.\} and Ming Xian",

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journal = "Organic Letters",

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T2 - One-pot syntheses of 2,3-disubstituted furans and thiophenes

AU - Devarie-Baez, Nelmi O.

AU - Kim, Won Suk

AU - Smith, Amos B.

AU - Xian, Ming

PY - 2009/4/16

Y1 - 2009/4/16

N2 - Effective, one-pot syntheses of 2,3-disubstituted furans and thiophenes, exploiting 2-fert-butyldimethylsilyl-3-formylfuran and -thiophene as the respective Afunctional linchpins, have been developed. The synthetic protocol involves multicomponent type II Anion Relay Chemistry (ARC) mediated by a solvent-controlled C(sp 2)→0 1,4-Brook rearrangement. Simple organolithiums and α-disubstituted ester enolates prove effective as the initiating nucleophiles.

AB - Effective, one-pot syntheses of 2,3-disubstituted furans and thiophenes, exploiting 2-fert-butyldimethylsilyl-3-formylfuran and -thiophene as the respective Afunctional linchpins, have been developed. The synthetic protocol involves multicomponent type II Anion Relay Chemistry (ARC) mediated by a solvent-controlled C(sp 2)→0 1,4-Brook rearrangement. Simple organolithiums and α-disubstituted ester enolates prove effective as the initiating nucleophiles.

UR - https://www.scopus.com/pages/publications/65249175226

U2 - 10.1021/ol900434k

DO - 10.1021/ol900434k

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JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

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

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