Selective Synthesis of Six Products from a Single Indolyl α-Diazocarbonyl Precursor

Michael J. James; Peter O'brien; Richard J. K. Taylor; William P. Unsworth

doi:10.1002/anie.201605337

Selective Synthesis of Six Products from a Single Indolyl α-Diazocarbonyl Precursor

Michael J. James
, Peter O'brien
, Richard J. K. Taylor
, William P. Unsworth

Organic Chemistry Group

University of York
University of York

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

Abstract

Indolyl α-diazocarbonyls can be selectively cyclized to give six distinct products through the careful choice of catalyst and reaction conditions. A range of catalysts were used, including complexes of RhII, PdII, and CuII, as well as SiO₂, to promote diazo decomposition and subsequent cyclization/rearrangement through a range of mechanistic pathways.

Original language	English
Pages (from-to)	9671-9675
Number of pages	5
Journal	Angewandte Chemie International Edition
Volume	55
Issue number	33
DOIs	https://doi.org/10.1002/anie.201605337
Publication status	Published - 20 Jul 2016

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title = "Selective Synthesis of Six Products from a Single Indolyl α-Diazocarbonyl Precursor",

abstract = "Indolyl α-diazocarbonyls can be selectively cyclized to give six distinct products through the careful choice of catalyst and reaction conditions. A range of catalysts were used, including complexes of RhII, PdII, and CuII, as well as SiO2, to promote diazo decomposition and subsequent cyclization/rearrangement through a range of mechanistic pathways.",

author = "James, \{Michael J.\} and Peter O'brien and Taylor, \{Richard J. K.\} and Unsworth, \{William P.\}",

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AU - James, Michael J.

AU - O'brien, Peter

AU - Taylor, Richard J. K.

AU - Unsworth, William P.

PY - 2016/7/20

Y1 - 2016/7/20

N2 - Indolyl α-diazocarbonyls can be selectively cyclized to give six distinct products through the careful choice of catalyst and reaction conditions. A range of catalysts were used, including complexes of RhII, PdII, and CuII, as well as SiO2, to promote diazo decomposition and subsequent cyclization/rearrangement through a range of mechanistic pathways.

AB - Indolyl α-diazocarbonyls can be selectively cyclized to give six distinct products through the careful choice of catalyst and reaction conditions. A range of catalysts were used, including complexes of RhII, PdII, and CuII, as well as SiO2, to promote diazo decomposition and subsequent cyclization/rearrangement through a range of mechanistic pathways.

U2 - 10.1002/anie.201605337

DO - 10.1002/anie.201605337

M3 - Article

SN - 1433-7851

VL - 55

SP - 9671

EP - 9675

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 33

ER -

Selective Synthesis of Six Products from a Single Indolyl α-Diazocarbonyl Precursor

Abstract

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