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Title: Metal-Free Cross-Coupling of $$\pi$$-Conjugated Triazenes with Unactivated Arenes via Photoactivation

Journal Article · · Organic Chemistry Frontiers (Online)
DOI: https://doi.org/10.1039/C8QO00938D · OSTI ID:1544131
 [1];  [1]; ORCiD logo [2]; ORCiD logo [2]; ORCiD logo [1]
  1. Univ. of Texas, Arlington, TX (United States)
  2. Univ. of Colorado, Denver, CO (United States)
+ Show Author Affiliations

Cross-coupling of aryl compounds is one of the most powerful carbon–carbon bond forming reactions available. However, the vast majority employ scarce and expensive transition metal salts, in combination with high temperatures and long reaction times. In this article, we report a new, metal-free biaryl coupling that includes photoactivation of π-conjugated triazenes, in the presence of unactivated arenes, carried out at room temperature. Key experiments and theoretical calculations, to elucidate mechanistic details of this new, direct and significantly milder synthetic approach are presented.

Research Organization:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC)
Sponsoring Organization:
National Science Foundation (NSF); USDOE Office of Science (SC)
Grant/Contract Number:
AC02-05CH11231
OSTI ID:
1544131
Journal Information:
Organic Chemistry Frontiers (Online), Journal Name: Organic Chemistry Frontiers (Online) Journal Issue: 2 Vol. 6; ISSN OCFRA8; ISSN 2052-4129
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

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Cited By (4)

π‐Conjugated Triazenes and Nitriles: Simple Photoinduced Synthesis of Anilides Using Mild and Metal‐Free Conditions journal January 2020
π‐Conjugated Triazenes and Nitriles: Simple Photoinduced Synthesis of Anilides Using Mild and Metal‐Free Conditions journal March 2020
Modifications of amino acids using arenediazonium salts journal January 2019
Brønsted and Lewis acid adducts of triazenes journal January 2020

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