Contra-Friedel-Crafts tert-butylation of substituted aromatic rings via directed metallation and sulfinylation

Jonathan Clayden; Christopher C. Stimson; Martine Keenan

doi:10.1039/b600181e

Contra-Friedel-Crafts tert-butylation of substituted aromatic rings via directed metallation and sulfinylation

Jonathan Clayden^*, Christopher C. Stimson, Martine Keenan

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

26 Citations (Scopus)

Abstract

Directed metallation and sulfinylation yields sulfoxides which undergo ipso nucleophilic aromatic substitution with tertiary and secondary alkyllithiums, giving aromatic rings bearing alkyl groups generally incompatible with directed metallation methods and with regioselectivity complementary with classical Friedel-Crafts substitution.

Original language	English
Pages (from-to)	1393-1394
Number of pages	2
Journal	Chemical Communications
Issue number	13
Early online date	21 Feb 2006
DOIs	https://doi.org/10.1039/b600181e
Publication status	Published - 7 Apr 2006

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title = "Contra-Friedel-Crafts tert-butylation of substituted aromatic rings via directed metallation and sulfinylation",

abstract = "Directed metallation and sulfinylation yields sulfoxides which undergo ipso nucleophilic aromatic substitution with tertiary and secondary alkyllithiums, giving aromatic rings bearing alkyl groups generally incompatible with directed metallation methods and with regioselectivity complementary with classical Friedel-Crafts substitution.",

author = "Jonathan Clayden and Stimson, {Christopher C.} and Martine Keenan",

year = "2006",

month = apr,

day = "7",

doi = "10.1039/b600181e",

language = "English",

pages = "1393--1394",

journal = "Chemical Communications",

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T1 - Contra-Friedel-Crafts tert-butylation of substituted aromatic rings via directed metallation and sulfinylation

AU - Clayden, Jonathan

AU - Stimson, Christopher C.

AU - Keenan, Martine

PY - 2006/4/7

Y1 - 2006/4/7

N2 - Directed metallation and sulfinylation yields sulfoxides which undergo ipso nucleophilic aromatic substitution with tertiary and secondary alkyllithiums, giving aromatic rings bearing alkyl groups generally incompatible with directed metallation methods and with regioselectivity complementary with classical Friedel-Crafts substitution.

AB - Directed metallation and sulfinylation yields sulfoxides which undergo ipso nucleophilic aromatic substitution with tertiary and secondary alkyllithiums, giving aromatic rings bearing alkyl groups generally incompatible with directed metallation methods and with regioselectivity complementary with classical Friedel-Crafts substitution.

UR - http://www.scopus.com/inward/record.url?scp=33645036768&partnerID=8YFLogxK

U2 - 10.1039/b600181e

DO - 10.1039/b600181e

M3 - Article (Academic Journal)

C2 - 16550277

AN - SCOPUS:33645036768

SN - 1359-7345

SP - 1393

EP - 1394

JO - Chemical Communications

JF - Chemical Communications

IS - 13

ER -

Contra-Friedel-Crafts tert-butylation of substituted aromatic rings via directed metallation and sulfinylation

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