Regioselective heterohalogenation of 4-halo-anisoles via a series of sequential ortho-aluminations and electrophilic halogenations

Benjamin Grant Conway; Elaine Crosbie; Alan Kennedy; Robert E. Mulvey; Stuart D. Robertson

doi:10.1039/c2cc30795b

Regioselective heterohalogenation of 4-halo-anisoles via a series of sequential ortho-aluminations and electrophilic halogenations

Benjamin Grant Conway, Elaine Crosbie, Alan Kennedy, Robert E. Mulvey, Stuart D. Robertson

Pure And Applied Chemistry

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

24 Citations (Scopus)

Abstract

As the aluminate base [LiAl(TMP)(2)(iBu)(2)] 1 displays halogen tolerance towards substituted aromatics, 4-halo-anisoles have been ortho-aluminated and electrophilically quenched to form synthetically useful multi-heterohalogenated anisoles, with the Al intermediates along the route structurally defined.

Original language	English
Pages (from-to)	4674-4676
Number of pages	3
Journal	Chemical Communications
Volume	48
Issue number	39
DOIs	https://doi.org/10.1039/c2cc30795b
Publication status	Published - 2012

Keywords

halogen tolerance
heterohalogenation

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10.1039/c2cc30795b

Cite this

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title = "Regioselective heterohalogenation of 4-halo-anisoles via a series of sequential ortho-aluminations and electrophilic halogenations",

abstract = "As the aluminate base [LiAl(TMP)(2)(iBu)(2)] 1 displays halogen tolerance towards substituted aromatics, 4-halo-anisoles have been ortho-aluminated and electrophilically quenched to form synthetically useful multi-heterohalogenated anisoles, with the Al intermediates along the route structurally defined.",

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language = "English",

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pages = "4674--4676",

journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

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AU - Crosbie, Elaine

AU - Kennedy, Alan

AU - Mulvey, Robert E.

AU - Robertson, Stuart D.

PY - 2012

Y1 - 2012

N2 - As the aluminate base [LiAl(TMP)(2)(iBu)(2)] 1 displays halogen tolerance towards substituted aromatics, 4-halo-anisoles have been ortho-aluminated and electrophilically quenched to form synthetically useful multi-heterohalogenated anisoles, with the Al intermediates along the route structurally defined.

AB - As the aluminate base [LiAl(TMP)(2)(iBu)(2)] 1 displays halogen tolerance towards substituted aromatics, 4-halo-anisoles have been ortho-aluminated and electrophilically quenched to form synthetically useful multi-heterohalogenated anisoles, with the Al intermediates along the route structurally defined.

KW - halogen tolerance

KW - heterohalogenation

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U2 - 10.1039/c2cc30795b

DO - 10.1039/c2cc30795b

M3 - Article

SN - 1359-7345

VL - 48

SP - 4674

EP - 4676

JO - Chemical Communications

JF - Chemical Communications

IS - 39

ER -

Regioselective heterohalogenation of 4-halo-anisoles via a series of sequential ortho-aluminations and electrophilic halogenations

Abstract

Keywords

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EXPLOITING SYNTHETIC AND STRUCTURAL SYNERGISM IN ALKALI-METAL-MEDIATED ORGANOTRANSITIONMETALLATION (AMMO)

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

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Regioselective heterohalogenation of 4-halo-anisoles via a series of sequential ortho-aluminations and electrophilic halogenations

Abstract

Keywords

Access to Document

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Projects

EXPLOITING SYNTHETIC AND STRUCTURAL SYNERGISM IN ALKALI-METAL-MEDIATED ORGANOTRANSITIONMETALLATION (AMMO)

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

Cite this