Desulfonylation of amides using tributyltin hydride, samarium diiodide or zinc/titanium tetrachloride. A comparison of methods

H S  Knowles; A F  Parsons; R M  Pettifer; S  Rickling

Desulfonylation of amides using tributyltin hydride, samarium diiodide or zinc/titanium tetrachloride. A comparison of methods

H S Knowles, A F Parsons, R M Pettifer, S Rickling

Chemistry

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

Abstract

Deprotection of N-sulfonylated amides can be achieved by reaction with Bu3SnH, SmI2 or TiCl4/Zn. All three methods gave good yields (typically >60%) when using N-benzoyl or related amides while the corresponding N-acetyl derivatives proved to be inert to deprotection under the same reaction conditions. The mechanistic implications of this are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	979-988
Number of pages	10
Journal	Tetrahedron
Volume	56
Issue number	7
Publication status	Published - 11 Feb 2000

Keywords

amides
samarium and compounds
tin and compounds
titanium and compounds
BETA-KETO PHENYLSULFONES
RADICAL CYCLIZATION
ORGANIC-SYNTHESIS
IODIDE
SULFONAMIDES
EFFICIENT
CLEAVAGE
ROUTE
REDUCTION
REMOVAL

Cite this

@article{b95e43accd5648158b723e6055db880f,

title = "Desulfonylation of amides using tributyltin hydride, samarium diiodide or zinc/titanium tetrachloride. A comparison of methods",

abstract = "Deprotection of N-sulfonylated amides can be achieved by reaction with Bu3SnH, SmI2 or TiCl4/Zn. All three methods gave good yields (typically >60%) when using N-benzoyl or related amides while the corresponding N-acetyl derivatives proved to be inert to deprotection under the same reaction conditions. The mechanistic implications of this are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.",

keywords = "amides, samarium and compounds, tin and compounds, titanium and compounds, BETA-KETO PHENYLSULFONES, RADICAL CYCLIZATION, ORGANIC-SYNTHESIS, IODIDE, SULFONAMIDES, EFFICIENT, CLEAVAGE, ROUTE, REDUCTION, REMOVAL",

author = "Knowles, {H S} and Parsons, {A F} and Pettifer, {R M} and S Rickling",

year = "2000",

month = feb,

day = "11",

language = "English",

volume = "56",

pages = "979--988",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "7",

}

TY - JOUR

T1 - Desulfonylation of amides using tributyltin hydride, samarium diiodide or zinc/titanium tetrachloride. A comparison of methods

AU - Knowles, H S

AU - Parsons, A F

AU - Pettifer, R M

AU - Rickling, S

PY - 2000/2/11

Y1 - 2000/2/11

N2 - Deprotection of N-sulfonylated amides can be achieved by reaction with Bu3SnH, SmI2 or TiCl4/Zn. All three methods gave good yields (typically >60%) when using N-benzoyl or related amides while the corresponding N-acetyl derivatives proved to be inert to deprotection under the same reaction conditions. The mechanistic implications of this are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

AB - Deprotection of N-sulfonylated amides can be achieved by reaction with Bu3SnH, SmI2 or TiCl4/Zn. All three methods gave good yields (typically >60%) when using N-benzoyl or related amides while the corresponding N-acetyl derivatives proved to be inert to deprotection under the same reaction conditions. The mechanistic implications of this are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

KW - amides

KW - samarium and compounds

KW - tin and compounds

KW - titanium and compounds

KW - BETA-KETO PHENYLSULFONES

KW - RADICAL CYCLIZATION

KW - ORGANIC-SYNTHESIS

KW - IODIDE

KW - SULFONAMIDES

KW - EFFICIENT

KW - CLEAVAGE

KW - ROUTE

KW - REDUCTION

KW - REMOVAL

M3 - Article

SN - 0040-4020

VL - 56

SP - 979

EP - 988

JO - Tetrahedron

JF - Tetrahedron

IS - 7

ER -