Metal‐Free, Hindered, Regioselective Access to Multifunctional Groups Diarylamines via SNAr Substitution of P‐Nitroso Aromatic Methyl Ether by Arylamines
Multifunctional groups diarylamines, an innovative product, efficiently produced from arylamines and p‐nitrosoanisole derivatives by intermolecular SNAr under weak acid conditions. This SNAr proceeds under mild reaction conditions, and more significantly, the substrates involved do not necessarily r...
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| Published in | Chemistry : a European journal Vol. 30; no. 11 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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21.02.2024
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| Abstract | Multifunctional groups diarylamines, an innovative product, efficiently produced from arylamines and p‐nitrosoanisole derivatives by intermolecular SNAr under weak acid conditions. This SNAr proceeds under mild reaction conditions, and more significantly, the substrates involved do not necessarily require strong electron‐withdrawing groups. Moreover, this SNAr is characterized by resistance to space crowding, tolerance to halogen and nitroso functional groups, and high regioselectivity. Mechanistic observations suggest that the SNAr is the result of the transfer of the positive charge center of the protonated nitroso group to the p‐methoxy group.
Multifunctional groups diarylamines efficiently produced from arylamines and p‐nitrosoanisole derivatives by intermolecular SNAr under weak acid conditions. Relying on the catalysis of hydrogen protons, the SNAr reaction, which is endowed with resistance to space crowding, tolerance to halogen and nitroso groups, and high regioselectivity, can be carried out under mild conditions, even if the substrates involved do not have strong electron‐withdrawing groups. |
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| AbstractList | Multifunctional groups diarylamines, an innovative product, efficiently produced from arylamines and p‐nitrosoanisole derivatives by intermolecular SNAr under weak acid conditions. This SNAr proceeds under mild reaction conditions, and more significantly, the substrates involved do not necessarily require strong electron‐withdrawing groups. Moreover, this SNAr is characterized by resistance to space crowding, tolerance to halogen and nitroso functional groups, and high regioselectivity. Mechanistic observations suggest that the SNAr is the result of the transfer of the positive charge center of the protonated nitroso group to the p‐methoxy group. Multifunctional groups diarylamines, an innovative product, efficiently produced from arylamines and p‐nitrosoanisole derivatives by intermolecular SNAr under weak acid conditions. This SNAr proceeds under mild reaction conditions, and more significantly, the substrates involved do not necessarily require strong electron‐withdrawing groups. Moreover, this SNAr is characterized by resistance to space crowding, tolerance to halogen and nitroso functional groups, and high regioselectivity. Mechanistic observations suggest that the SNAr is the result of the transfer of the positive charge center of the protonated nitroso group to the p‐methoxy group. Multifunctional groups diarylamines efficiently produced from arylamines and p‐nitrosoanisole derivatives by intermolecular SNAr under weak acid conditions. Relying on the catalysis of hydrogen protons, the SNAr reaction, which is endowed with resistance to space crowding, tolerance to halogen and nitroso groups, and high regioselectivity, can be carried out under mild conditions, even if the substrates involved do not have strong electron‐withdrawing groups. |
| Author | Liu, Bing Li, Yutao Wu, Qin Zhao, Tianming Zhang, Yazhou Ma, Xianguo Zou, Shuliang |
| Author_xml | – sequence: 1 givenname: Shuliang orcidid: 0000-0001-5146-0486 surname: Zou fullname: Zou, Shuliang email: slzou@git.edu.cn organization: Guizhou Institute of Technology – sequence: 2 givenname: Yazhou surname: Zhang fullname: Zhang, Yazhou organization: Guizhou University of Traditional Chinese Medicine – sequence: 3 givenname: Qin surname: Wu fullname: Wu, Qin organization: Guizhou Institute of Technology – sequence: 4 givenname: Tianming surname: Zhao fullname: Zhao, Tianming organization: Guizhou Institute of Technology – sequence: 5 givenname: Yutao surname: Li fullname: Li, Yutao organization: Guizhou Institute of Technology – sequence: 6 givenname: Bing surname: Liu fullname: Liu, Bing organization: Guizhou Institute of Technology – sequence: 7 givenname: Xianguo surname: Ma fullname: Ma, Xianguo email: maxianguo@git.edu.cn organization: Guizhou Institute of Technology |
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| Keywords | ACTIVATION nitroso arenes ARYL ETHERS ETHERIFICATION BOND-CLEAVAGE hindered regioselective KETONES CROSS-COUPLINGS intermolecular nucleophilic aromatic substitution CHEMISTRY amination DERIVATIVES |
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| Snippet | Multifunctional groups diarylamines, an innovative product, efficiently produced from arylamines and p‐nitrosoanisole derivatives by intermolecular SNAr under... Multifunctional groups diarylamines, an innovative product, efficiently produced from arylamines and p-nitrosoanisole derivatives by intermolecular SNAr under... |
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| Title | Metal‐Free, Hindered, Regioselective Access to Multifunctional Groups Diarylamines via SNAr Substitution of P‐Nitroso Aromatic Methyl Ether by Arylamines |
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