Protic solvent-promoted neutral allylation of aldehydes and ketones with 1,8-bis(allylstannyl)naphthalenes

Naoki Asao; Noriko Abe; Zheng Tan; Keiji Maruoka

doi:10.1055/s-1998-1679

Protic solvent-promoted neutral allylation of aldehydes and ketones with 1,8-bis(allylstannyl)naphthalenes

Naoki Asao, Noriko Abe, Zheng Tan, Keiji Maruoka

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

7 Citations (Scopus)

Abstract

The allylation reactions of carbonyl compounds using 1,8-bis(dibutylstannyl)naphthalene 1 (R = Bu) were dramatically promoted by using a mixture of THF and CF₃CH₂OH (5 : 1) as solvent. The rate acceleration was due to the enhancement of the Brønsted acidity of CF₃CH₂OH by the formation of the chelate complex 6 (R = CH₂CF₃) resulting from the chelation effect of two neighboring tin atoms.

Original language	English
Pages (from-to)	377-378
Number of pages	2
Journal	Synlett
Issue number	4
DOIs	https://doi.org/10.1055/s-1998-1679
Publication status	Published - 1998 Apr

ASJC Scopus subject areas

Organic Chemistry

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abstract = "The allylation reactions of carbonyl compounds using 1,8-bis(dibutylstannyl)naphthalene 1 (R = Bu) were dramatically promoted by using a mixture of THF and CF3CH2OH (5 : 1) as solvent. The rate acceleration was due to the enhancement of the Br{\o}nsted acidity of CF3CH2OH by the formation of the chelate complex 6 (R = CH2CF3) resulting from the chelation effect of two neighboring tin atoms.",

author = "Naoki Asao and Noriko Abe and Zheng Tan and Keiji Maruoka",

year = "1998",

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AU - Abe, Noriko

AU - Tan, Zheng

AU - Maruoka, Keiji

PY - 1998/4

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AB - The allylation reactions of carbonyl compounds using 1,8-bis(dibutylstannyl)naphthalene 1 (R = Bu) were dramatically promoted by using a mixture of THF and CF3CH2OH (5 : 1) as solvent. The rate acceleration was due to the enhancement of the Brønsted acidity of CF3CH2OH by the formation of the chelate complex 6 (R = CH2CF3) resulting from the chelation effect of two neighboring tin atoms.

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SN - 0936-5214

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ER -

Protic solvent-promoted neutral allylation of aldehydes and ketones with 1,8-bis(allylstannyl)naphthalenes

Abstract

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