New lithium-zincate approaches for the selective functionalisation of pyrazine: direct dideprotozincation vs. nucleophilic alkylation

Sharon E. Baillie; Victoria L. Blair; David C. Blakemore; Duncan Hay; Alan Kennedy; David C. Pryde; Eva Hevia

doi:10.1039/c2cc16959b

New lithium-zincate approaches for the selective functionalisation of pyrazine: direct dideprotozincation vs. nucleophilic alkylation

Sharon E. Baillie, Victoria L. Blair, David C. Blakemore, Duncan Hay, Alan Kennedy, David C. Pryde, Eva Hevia

Pure And Applied Chemistry

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

40 Citations (Scopus)

Abstract

Comparing the reactivity of the related lithium zincates [(THF)LiZn(TMP)Bu-t(2)] (1) and [(PMDETA)(LiZnBu3)-Bu-t] (2) towards pyrazine discloses two new bimetallic approaches for the selective 2,5-dideprotonation and room temperature C-H alkylation of this sensitive heterocycle.

Original language	English
Pages (from-to)	1985-1987
Number of pages	3
Journal	Chemical Communications
Volume	48
Issue number	14
DOIs	https://doi.org/10.1039/c2cc16959b
Publication status	Published - 2012

Keywords

functionalisation
pyrazine
dideprotozincation
nucleophilic alkylation

Access to Document

10.1039/c2cc16959b

Cite this

@article{68206ef263734c598a77fa6fa03ccbd4,

title = "New lithium-zincate approaches for the selective functionalisation of pyrazine: direct dideprotozincation vs. nucleophilic alkylation",

abstract = "Comparing the reactivity of the related lithium zincates [(THF)LiZn(TMP)Bu-t(2)] (1) and [(PMDETA)(LiZnBu3)-Bu-t] (2) towards pyrazine discloses two new bimetallic approaches for the selective 2,5-dideprotonation and room temperature C-H alkylation of this sensitive heterocycle.",

keywords = "functionalisation , pyrazine, dideprotozincation , nucleophilic alkylation",

author = "Baillie, {Sharon E.} and Blair, {Victoria L.} and Blakemore, {David C.} and Duncan Hay and Alan Kennedy and Pryde, {David C.} and Eva Hevia",

year = "2012",

doi = "10.1039/c2cc16959b",

language = "English",

volume = "48",

pages = "1985--1987",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "14",

}

TY - JOUR

T1 - New lithium-zincate approaches for the selective functionalisation of pyrazine: direct dideprotozincation vs. nucleophilic alkylation

AU - Baillie, Sharon E.

AU - Blair, Victoria L.

AU - Blakemore, David C.

AU - Hay, Duncan

AU - Kennedy, Alan

AU - Pryde, David C.

AU - Hevia, Eva

PY - 2012

Y1 - 2012

N2 - Comparing the reactivity of the related lithium zincates [(THF)LiZn(TMP)Bu-t(2)] (1) and [(PMDETA)(LiZnBu3)-Bu-t] (2) towards pyrazine discloses two new bimetallic approaches for the selective 2,5-dideprotonation and room temperature C-H alkylation of this sensitive heterocycle.

AB - Comparing the reactivity of the related lithium zincates [(THF)LiZn(TMP)Bu-t(2)] (1) and [(PMDETA)(LiZnBu3)-Bu-t] (2) towards pyrazine discloses two new bimetallic approaches for the selective 2,5-dideprotonation and room temperature C-H alkylation of this sensitive heterocycle.

KW - functionalisation

KW - pyrazine

KW - dideprotozincation

KW - nucleophilic alkylation

UR - http://www.scopus.com/inward/record.url?scp=84856498746&partnerID=8YFLogxK

U2 - 10.1039/c2cc16959b

DO - 10.1039/c2cc16959b

M3 - Article

SN - 1359-7345

VL - 48

SP - 1985

EP - 1987

JO - Chemical Communications

JF - Chemical Communications

IS - 14

ER -

New lithium-zincate approaches for the selective functionalisation of pyrazine: direct dideprotozincation vs. nucleophilic alkylation

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

Cite this

New lithium-zincate approaches for the selective functionalisation of pyrazine: direct dideprotozincation vs. nucleophilic alkylation

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Projects

Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

Cite this