Modifying alkylzinc reactivity with 2,2 '-dipyridylamide: activation of tBu-Zn bonds for para-alkylation of benzophenone

David R. Armstrong; Jennifer A. Garden; Alan Kennedy; Robert Mulvey; Stuart D. Robertson

doi:10.1002/anie.201302426

Modifying alkylzinc reactivity with 2,2 '-dipyridylamide: activation of tBu-Zn bonds for para-alkylation of benzophenone

David R. Armstrong, Jennifer A. Garden, Alan Kennedy, Robert Mulvey, Stuart D. Robertson

Pure And Applied Chemistry

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

20 Citations (Scopus)

59 Downloads (Pure)

Abstract

Undercover agent: Masquerading as a simple donor-acceptor complex (1), sodium amide substoichiometrically activates tBuZn for the challenging 1,6-addition of a tert-butyl group to benzophenone. In contrast, the nonactivated tBuZn is ineffectual.

Original language	English
Pages (from-to)	7190-7193
Number of pages	4
Journal	Angewandte Chemie International Edition
Volume	52
Issue number	28
Early online date	5 Jun 2013
DOIs	https://doi.org/10.1002/anie.201302426
Publication status	Published - 8 Jul 2013

Keywords

zinc
reagents
ligands
alkylation
metalation
alkali metal
crystal-structure
dipyridylamine
chloride
2,2-dipyridylamine
sodium TMP-zincate
chemistry
homogeneous catalysis
amides
complexes

Access to Document

10.1002/anie.201302426Licence: CC BY 4.0

Armstrong-etal-Angewandte2013-modifying-alkylzincFinal published version, 541 KBLicence: CC BY 4.0

A co-operative bimetallic approach for the transformation of lithiation
Mulvey, R.
EPSRC (Engineering and Physical Sciences Research Council)
1/03/13 → 29/02/16
Project: Research

x-ray diffractometer
Alan Kennedy
Pure And Applied Chemistry
Facility/equipment: Equipment

Cite this

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title = "Modifying alkylzinc reactivity with 2,2 '-dipyridylamide: activation of tBu-Zn bonds for para-alkylation of benzophenone",

abstract = "Undercover agent: Masquerading as a simple donor-acceptor complex (1), sodium amide substoichiometrically activates tBuZn for the challenging 1,6-addition of a tert-butyl group to benzophenone. In contrast, the nonactivated tBuZn is ineffectual. ",

keywords = "zinc, reagents, ligands, alkylation, metalation, alkali metal, crystal-structure, dipyridylamine, chloride, 2,2-dipyridylamine, sodium TMP-zincate, chemistry, homogeneous catalysis, amides, complexes",

author = "Armstrong, {David R.} and Garden, {Jennifer A.} and Alan Kennedy and Robert Mulvey and Robertson, {Stuart D.}",

year = "2013",

month = jul,

day = "8",

doi = "10.1002/anie.201302426",

language = "English",

volume = "52",

pages = "7190--7193",

journal = "Angewandte Chemie International Edition",

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number = "28",

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T1 - Modifying alkylzinc reactivity with 2,2 '-dipyridylamide

T2 - activation of tBu-Zn bonds for para-alkylation of benzophenone

AU - Armstrong, David R.

AU - Garden, Jennifer A.

AU - Kennedy, Alan

AU - Mulvey, Robert

AU - Robertson, Stuart D.

PY - 2013/7/8

Y1 - 2013/7/8

N2 - Undercover agent: Masquerading as a simple donor-acceptor complex (1), sodium amide substoichiometrically activates tBuZn for the challenging 1,6-addition of a tert-butyl group to benzophenone. In contrast, the nonactivated tBuZn is ineffectual.

AB - Undercover agent: Masquerading as a simple donor-acceptor complex (1), sodium amide substoichiometrically activates tBuZn for the challenging 1,6-addition of a tert-butyl group to benzophenone. In contrast, the nonactivated tBuZn is ineffectual.

KW - zinc

KW - reagents

KW - ligands

KW - alkylation

KW - metalation

KW - alkali metal

KW - crystal-structure

KW - dipyridylamine

KW - chloride

KW - 2,2-dipyridylamine

KW - sodium TMP-zincate

KW - chemistry

KW - homogeneous catalysis

KW - amides

KW - complexes

U2 - 10.1002/anie.201302426

DO - 10.1002/anie.201302426

M3 - Article

C2 - 23740807

SN - 1433-7851

VL - 52

SP - 7190

EP - 7193

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 28

ER -

Modifying alkylzinc reactivity with 2,2 '-dipyridylamide: activation of tBu-Zn bonds for para-alkylation of benzophenone

Abstract

Keywords

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Projects

A co-operative bimetallic approach for the transformation of lithiation

Equipment

x-ray diffractometer

Cite this