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

TY - JOUR

T1 - Selective Synthesis of Six Products from a Single Indolyl α-Diazocarbonyl Precursor

AU - James, Michael J.

AU - O'Brien, Peter

AU - Taylor, Richard J K

AU - Unsworth, William P.

N1 - © 2016 Wiley-VCH Verlag GmbH & Co. K. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details. Embargo period : 12 months

PY - 2016/8/8

Y1 - 2016/8/8

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 Rh(II) , Pd(II) , and Cu(II) , 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 Rh(II) , Pd(II) , and Cu(II) , as well as SiO2 , to promote diazo decomposition and subsequent cyclization/rearrangement through a range of mechanistic pathways.

KW - cyclizations

KW - diazo compounds

KW - indoles

KW - spirocycles

KW - synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=84978743860&partnerID=8YFLogxK

U2 - 10.1002/anie.201605337

DO - 10.1002/anie.201605337

M3 - Article

C2 - 27435296

SN - 1433-7851

VL - 55

SP - 9671

EP - 9675

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 33

ER -