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  4. Synthesis of Indenyl Triazenes by Rhodium-Catalyzed Annulation Reactions
 
research article

Synthesis of Indenyl Triazenes by Rhodium-Catalyzed Annulation Reactions

Bormann, Carl T.  
•
Abela, Florian G.
•
Scopelliti, Rosario  
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March 25, 2020
European Journal of Organic Chemistry

The synthesis of vinyl triazenes by metal-catalyzed processes is attractive, but only few examples have been described so far. Here, we describe Rh-catalyzed [3+2] annulation reactions of arylboronic acid derivatives and alkynyl triazenes. These reactions provide access to functionalized indenyl triazenes. The regioselectivity of the annulations is mostly high, but strongly dependent on the substituents on the alkyne. The triazene group in the products can be cleaved under acidic condition. In contrast to what has been reported for other vinyl triazenes, rearrangements are observed instead of direct substitution reactions.

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Type
research article
DOI
10.1002/ejoc.202000195
Web of Science ID

WOS:000521400700001

Author(s)
Bormann, Carl T.  
Abela, Florian G.
Scopelliti, Rosario  
Fadaei-Tirani, Farzaneh  
Severin, Kay  
Date Issued

2020-03-25

Published in
European Journal of Organic Chemistry
Issue

14

Start page

2130

End page

2139

Subjects

Chemistry, Organic

•

Chemistry

•

rhodium

•

triazenes

•

indene

•

homogeneous catalysis

•

alkynes

•

organoboron reagents

•

diazonium salts

•

vinyl cations

•

alkynes

•

rearrangement

•

solvolysis

•

c-14

•

aryltriazenes

•

cyclization

•

generation

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LCS  
Available on Infoscience
April 8, 2020
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/168016
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