Selective functionalization of an isodurene-Cr(CO)3 complex

Martin F. Semmelhack; G. Hilt

Selective functionalization of an isodurene-Cr(CO)₃ complex

Martin F. Semmelhack, G. Hilt

Chemistry

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

3 Scopus citations

Abstract

Two synthesis routes to thiol 1 from mesitylene were evaluated. A direct bromination of a 1,2,3,5-tetraalkylbenzene derivative (2) was relatively unselective and gave the desired bromide in 10% yield. Deprotonation of the corresponding Cr(CO)₃ complex with LiTMP and trapping with a bulky silane (Ph₂tBuSiCl) gave high selectivity for the desired position, apparently through equilibration of benzylic anions and a product-determining trapping step.

Original language	English (US)
Pages (from-to)	1127-1128
Number of pages	2
Journal	Synlett
Issue number	8
State	Published - Sep 4 2000

All Science Journal Classification (ASJC) codes

Organic Chemistry

Keywords

Arene complexes
Metallation
Organometallic chemistry
Regioselectivity

Cite this

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title = "Selective functionalization of an isodurene-Cr(CO)3 complex",

abstract = "Two synthesis routes to thiol 1 from mesitylene were evaluated. A direct bromination of a 1,2,3,5-tetraalkylbenzene derivative (2) was relatively unselective and gave the desired bromide in 10% yield. Deprotonation of the corresponding Cr(CO)3 complex with LiTMP and trapping with a bulky silane (Ph2tBuSiCl) gave high selectivity for the desired position, apparently through equilibration of benzylic anions and a product-determining trapping step.",

keywords = "Arene complexes, Metallation, Organometallic chemistry, Regioselectivity",

author = "Semmelhack, {Martin F.} and G. Hilt",

year = "2000",

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language = "English (US)",

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journal = "Synlett",

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T1 - Selective functionalization of an isodurene-Cr(CO)3 complex

AU - Semmelhack, Martin F.

AU - Hilt, G.

PY - 2000/9/4

Y1 - 2000/9/4

N2 - Two synthesis routes to thiol 1 from mesitylene were evaluated. A direct bromination of a 1,2,3,5-tetraalkylbenzene derivative (2) was relatively unselective and gave the desired bromide in 10% yield. Deprotonation of the corresponding Cr(CO)3 complex with LiTMP and trapping with a bulky silane (Ph2tBuSiCl) gave high selectivity for the desired position, apparently through equilibration of benzylic anions and a product-determining trapping step.

AB - Two synthesis routes to thiol 1 from mesitylene were evaluated. A direct bromination of a 1,2,3,5-tetraalkylbenzene derivative (2) was relatively unselective and gave the desired bromide in 10% yield. Deprotonation of the corresponding Cr(CO)3 complex with LiTMP and trapping with a bulky silane (Ph2tBuSiCl) gave high selectivity for the desired position, apparently through equilibration of benzylic anions and a product-determining trapping step.

KW - Arene complexes

KW - Metallation

KW - Organometallic chemistry

KW - Regioselectivity

UR - http://www.scopus.com/inward/record.url?scp=0033874901&partnerID=8YFLogxK

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M3 - Article

AN - SCOPUS:0033874901

SN - 0936-5214

SP - 1127

EP - 1128

JO - Synlett

JF - Synlett

IS - 8

ER -

Selective functionalization of an isodurene-Cr(CO)₃ complex

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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