Ligand effects in the metal catalysed reactions of N-aryldiazoamides: Ylide formation vs. insertion reactions

C J  Moody; S  Miah; A M Z  Slawin; D J  Mansfield; I C  Richards

Ligand effects in the metal catalysed reactions of N-aryldiazoamides: Ylide formation vs. insertion reactions

C J Moody, S Miah, A M Z Slawin, D J Mansfield, I C Richards

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

Abstract

Diazoamides 1a and 1b were prepared from 2-(O-allyl)- and 2-(S-allyl) anilines 2 respectively. Copper(II) catalysed decomposition of 1 resulted in formation of benzofused heterocycles 7 by [2,3]-rearrangement of the intermediate ylide. Rhodium(II) perfluorbutyramide catalysed reaction, however, gave mainly the indoles 8, 9 whereas rhodium(II) acetate catalysed reaction resulted in a mixture of products, with p-lactams formed by intramolecular C-H insertion predominating. Catalysed decomposition of N-pyridyl diazoamide 13 gave the stable pyridinium ylide 14, (C) 1998 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	9689-9700
Number of pages	12
Journal	Tetrahedron
Volume	54
Issue number	33
Publication status	Published - 13 Aug 1998

Keywords

carbenes and carbenoids
ylides
catalysis
C-H INSERTION
CARBON-HYDROGEN INSERTION
ALPHA-DIAZOCARBONYL COMPOUNDS
RHODIUM(II) CARBOXYLATE
ORGANIC-SYNTHESIS
CYCLOPENTANE CONSTRUCTION
STEREOSELECTIVE SYNTHESIS
CYCLOADDITION REACTIONS
CARBENOID REACTIONS
DIAZO-COMPOUNDS

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title = "Ligand effects in the metal catalysed reactions of N-aryldiazoamides: Ylide formation vs. insertion reactions",

abstract = "Diazoamides 1a and 1b were prepared from 2-(O-allyl)- and 2-(S-allyl) anilines 2 respectively. Copper(II) catalysed decomposition of 1 resulted in formation of benzofused heterocycles 7 by [2,3]-rearrangement of the intermediate ylide. Rhodium(II) perfluorbutyramide catalysed reaction, however, gave mainly the indoles 8, 9 whereas rhodium(II) acetate catalysed reaction resulted in a mixture of products, with p-lactams formed by intramolecular C-H insertion predominating. Catalysed decomposition of N-pyridyl diazoamide 13 gave the stable pyridinium ylide 14, (C) 1998 Elsevier Science Ltd. All rights reserved.",

keywords = "carbenes and carbenoids, ylides, catalysis, C-H INSERTION, CARBON-HYDROGEN INSERTION, ALPHA-DIAZOCARBONYL COMPOUNDS, RHODIUM(II) CARBOXYLATE, ORGANIC-SYNTHESIS, CYCLOPENTANE CONSTRUCTION, STEREOSELECTIVE SYNTHESIS, CYCLOADDITION REACTIONS, CARBENOID REACTIONS, DIAZO-COMPOUNDS",

author = "Moody, {C J} and S Miah and Slawin, {A M Z} and Mansfield, {D J} and Richards, {I C}",

year = "1998",

month = aug,

day = "13",

language = "English",

volume = "54",

pages = "9689--9700",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "33",

}

TY - JOUR

T1 - Ligand effects in the metal catalysed reactions of N-aryldiazoamides: Ylide formation vs. insertion reactions

AU - Moody, C J

AU - Miah, S

AU - Slawin, A M Z

AU - Mansfield, D J

AU - Richards, I C

PY - 1998/8/13

Y1 - 1998/8/13

N2 - Diazoamides 1a and 1b were prepared from 2-(O-allyl)- and 2-(S-allyl) anilines 2 respectively. Copper(II) catalysed decomposition of 1 resulted in formation of benzofused heterocycles 7 by [2,3]-rearrangement of the intermediate ylide. Rhodium(II) perfluorbutyramide catalysed reaction, however, gave mainly the indoles 8, 9 whereas rhodium(II) acetate catalysed reaction resulted in a mixture of products, with p-lactams formed by intramolecular C-H insertion predominating. Catalysed decomposition of N-pyridyl diazoamide 13 gave the stable pyridinium ylide 14, (C) 1998 Elsevier Science Ltd. All rights reserved.

AB - Diazoamides 1a and 1b were prepared from 2-(O-allyl)- and 2-(S-allyl) anilines 2 respectively. Copper(II) catalysed decomposition of 1 resulted in formation of benzofused heterocycles 7 by [2,3]-rearrangement of the intermediate ylide. Rhodium(II) perfluorbutyramide catalysed reaction, however, gave mainly the indoles 8, 9 whereas rhodium(II) acetate catalysed reaction resulted in a mixture of products, with p-lactams formed by intramolecular C-H insertion predominating. Catalysed decomposition of N-pyridyl diazoamide 13 gave the stable pyridinium ylide 14, (C) 1998 Elsevier Science Ltd. All rights reserved.

KW - carbenes and carbenoids

KW - ylides

KW - catalysis

KW - C-H INSERTION

KW - CARBON-HYDROGEN INSERTION

KW - ALPHA-DIAZOCARBONYL COMPOUNDS

KW - RHODIUM(II) CARBOXYLATE

KW - ORGANIC-SYNTHESIS

KW - CYCLOPENTANE CONSTRUCTION

KW - STEREOSELECTIVE SYNTHESIS

KW - CYCLOADDITION REACTIONS

KW - CARBENOID REACTIONS

KW - DIAZO-COMPOUNDS

M3 - Article

SN - 0040-4020

VL - 54

SP - 9689

EP - 9700

JO - Tetrahedron

JF - Tetrahedron

IS - 33

ER -

Ligand effects in the metal catalysed reactions of N-aryldiazoamides: Ylide formation vs. insertion reactions

Abstract

Keywords

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