Chemoselective debenzylation of N-benzyl tertiary amines with ceric ammonium nitrate

Steven D. Bull; Stephen G. Davies; Carry Fenton; Andrew W. Mulvaney; R. Shyam Prasad; Andrew D. Smith

doi:10.1039/b006852g

Chemoselective debenzylation of N-benzyl tertiary amines with ceric ammonium nitrate

Steven D. Bull, Stephen G. Davies^*, Carry Fenton, Andrew W. Mulvaney, R. Shyam Prasad, Andrew D. Smith

^*Corresponding author for this work

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

Abstract

Treatment of a range of N-benzyl tertiary amines with aqueous eerie ammonium nitrate results in N-debenzylation to afford the corresponding secondary amine. Chemoselective mono-W-debenzylation of N-benzyl tertiary amines is shown to occur in the presence of N-benzyl amides, O-benzyl ethers, O-benzyl esters, O-benzyl phenolates and 5-benzyl ethers.

Original language	English
Pages (from-to)	3765-3774
Number of pages	10
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	22
DOIs	https://doi.org/10.1039/b006852g
Publication status	Published - 1 Dec 2000

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title = "Chemoselective debenzylation of N-benzyl tertiary amines with ceric ammonium nitrate",

abstract = "Treatment of a range of N-benzyl tertiary amines with aqueous eerie ammonium nitrate results in N-debenzylation to afford the corresponding secondary amine. Chemoselective mono-W-debenzylation of N-benzyl tertiary amines is shown to occur in the presence of N-benzyl amides, O-benzyl ethers, O-benzyl esters, O-benzyl phenolates and 5-benzyl ethers.",

author = "Bull, {Steven D.} and Davies, {Stephen G.} and Carry Fenton and Mulvaney, {Andrew W.} and {Shyam Prasad}, R. and Smith, {Andrew D.}",

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T1 - Chemoselective debenzylation of N-benzyl tertiary amines with ceric ammonium nitrate

AU - Bull, Steven D.

AU - Davies, Stephen G.

AU - Fenton, Carry

AU - Mulvaney, Andrew W.

AU - Shyam Prasad, R.

AU - Smith, Andrew D.

PY - 2000/12/1

Y1 - 2000/12/1

N2 - Treatment of a range of N-benzyl tertiary amines with aqueous eerie ammonium nitrate results in N-debenzylation to afford the corresponding secondary amine. Chemoselective mono-W-debenzylation of N-benzyl tertiary amines is shown to occur in the presence of N-benzyl amides, O-benzyl ethers, O-benzyl esters, O-benzyl phenolates and 5-benzyl ethers.

AB - Treatment of a range of N-benzyl tertiary amines with aqueous eerie ammonium nitrate results in N-debenzylation to afford the corresponding secondary amine. Chemoselective mono-W-debenzylation of N-benzyl tertiary amines is shown to occur in the presence of N-benzyl amides, O-benzyl ethers, O-benzyl esters, O-benzyl phenolates and 5-benzyl ethers.

UR - http://www.scopus.com/inward/record.url?scp=0034700386&partnerID=8YFLogxK

U2 - 10.1039/b006852g

DO - 10.1039/b006852g

M3 - Article

AN - SCOPUS:0034700386

SN - 1470-4358

SP - 3765

EP - 3774

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 22

ER -

Chemoselective debenzylation of N-benzyl tertiary amines with ceric ammonium nitrate

Abstract

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