Transition-Metal-Free C–N Cross-Coupling Enabled by a Multifunctional ReagentClick to copy article linkArticle link copied!
- Patrick S. Fier*Patrick S. Fier*[email protected]Department of Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United StatesMore by Patrick S. Fier
- Suhong Kim*Suhong Kim*[email protected]Department of Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United StatesMore by Suhong Kim
Abstract
![Abstract Image](/cms/10.1021/jacs.4c00871/asset/images/medium/ja4c00871_0007.gif)
We report the design and development of a transition-metal-free cross-coupling reaction of phenols and primary amines using a simple and readily available multifunctional reagent. The reactions work by induced proximity and electronic activation of both the nucleophile and the electrophile for net dehydrative C–N coupling reactions. Notably, the reactions do not involve the use of a transition metal for C–N bond formation, preactivation of the phenol electrophile, or exclusion of air or moisture. The mild conditions tolerate a broad range of functional groups and allow for this to be applied to the late-stage functionalization of complex substrates with a wide scope of coupling partners.
Cited By
This article is cited by 2 publications.
- Matthew C. Carson, Cindy R. Liu, Yaning Liu, Marisa C. Kozlowski. Amination of Phenols and Halophenols via Pyridinium–Iridium Dual Photocatalysis. ACS Catalysis 2024, 14
(16)
, 12173-12180. https://doi.org/10.1021/acscatal.4c02797
- Kai Chen, Hang Shi. Nucleophilic Aromatic Substitution of Halobenzenes and Phenols with Catalysis by Arenophilic π Acids. Accounts of Chemical Research 2024, 57
(15)
, 2194-2206. https://doi.org/10.1021/acs.accounts.4c00327
Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.
Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.