Remote functionalisation via sodium alkylamidozincate intermediates: Access to unusual fluorenone and pyridyl ketone reactivity patterns

James J. Crawford; Ben J. Fleming; Alan R. Kennedy; Jan Klett; Charles T. O'Hara; Samantha A. Orr

doi:10.1039/c1cc10193e

Remote functionalisation via sodium alkylamidozincate intermediates: Access to unusual fluorenone and pyridyl ketone reactivity patterns

James J. Crawford, Ben J. Fleming, Alan R. Kennedy, Jan Klett, Charles T. O'Hara, Samantha A. Orr

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

19 Citations (Scopus)

Abstract

Treating fluorenone or 2-benzoylpyridine with the sodium zincate [(TMEDA)·Na(μ-^tBu)(μ-TMP)Zn(^tBu)] in hexane solution, gives efficient ^tBu addition across the respective organic substrate in a highly unusual 1,6-fashion, producing isolable organometallic intermediates which can be quenched and aerobically oxidised to give 3-tert-butyl-9H-fluoren-9-one and 2-benzoyl-5-tert-butylpyridine respectively.

Original language	English
Pages (from-to)	3772-3774
Number of pages	3
Journal	Chemical Communications
Volume	47
Issue number	13
DOIs	https://doi.org/10.1039/c1cc10193e
Publication status	Published - 7 Apr 2011
Externally published	Yes

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title = "Remote functionalisation via sodium alkylamidozincate intermediates: Access to unusual fluorenone and pyridyl ketone reactivity patterns",

abstract = "Treating fluorenone or 2-benzoylpyridine with the sodium zincate [(TMEDA)·Na(μ-tBu)(μ-TMP)Zn(tBu)] in hexane solution, gives efficient tBu addition across the respective organic substrate in a highly unusual 1,6-fashion, producing isolable organometallic intermediates which can be quenched and aerobically oxidised to give 3-tert-butyl-9H-fluoren-9-one and 2-benzoyl-5-tert-butylpyridine respectively.",

author = "Crawford, {James J.} and Fleming, {Ben J.} and Kennedy, {Alan R.} and Jan Klett and O'Hara, {Charles T.} and Orr, {Samantha A.}",

year = "2011",

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doi = "10.1039/c1cc10193e",

language = "English",

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T1 - Remote functionalisation via sodium alkylamidozincate intermediates

T2 - Access to unusual fluorenone and pyridyl ketone reactivity patterns

AU - Crawford, James J.

AU - Fleming, Ben J.

AU - Kennedy, Alan R.

AU - Klett, Jan

AU - O'Hara, Charles T.

AU - Orr, Samantha A.

PY - 2011/4/7

Y1 - 2011/4/7

N2 - Treating fluorenone or 2-benzoylpyridine with the sodium zincate [(TMEDA)·Na(μ-tBu)(μ-TMP)Zn(tBu)] in hexane solution, gives efficient tBu addition across the respective organic substrate in a highly unusual 1,6-fashion, producing isolable organometallic intermediates which can be quenched and aerobically oxidised to give 3-tert-butyl-9H-fluoren-9-one and 2-benzoyl-5-tert-butylpyridine respectively.

AB - Treating fluorenone or 2-benzoylpyridine with the sodium zincate [(TMEDA)·Na(μ-tBu)(μ-TMP)Zn(tBu)] in hexane solution, gives efficient tBu addition across the respective organic substrate in a highly unusual 1,6-fashion, producing isolable organometallic intermediates which can be quenched and aerobically oxidised to give 3-tert-butyl-9H-fluoren-9-one and 2-benzoyl-5-tert-butylpyridine respectively.

UR - http://www.scopus.com/inward/record.url?scp=79952633380&partnerID=8YFLogxK

U2 - 10.1039/c1cc10193e

DO - 10.1039/c1cc10193e

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VL - 47

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EP - 3774

JO - Chemical Communications

JF - Chemical Communications

IS - 13

ER -

Remote functionalisation via sodium alkylamidozincate intermediates: Access to unusual fluorenone and pyridyl ketone reactivity patterns

Abstract

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