Ceric Ammonium Nitrate Promoted Highly Chemo‐ and Regioselective ortho‐Nitration of Anilines under Mild Conditions. Issue 31 (16th August 2022)

• Record Type: Journal Article
• Authors: Iqbal, Zafar; Joshi, Asha; De, Saroj Ranjan
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 31(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-08-16
• Subjects: Aniline carbamates -- Ceric ammonium nitrate -- Nitrating agents -- Nitration reaction -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200746
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A new and practical strategy for chemo‐ and regioselective ortho ‐nitration of aniline carbamates under mild and neutral conditions have been disclosed using ceric ammonium nitrate (CAN) as a cheap nitrating agent. The electrophilic reaction exhibits a simple and straightforward pathway to obtain exclusively ortho ‐nitration products in good to excellent yields with outstanding functional groups tolerance for both electron rich and highly electron‐deficient anilines. The highlight of this protocol is the role of ceric ammonium nitrate (CAN) as a cheap nitrating agent that (Ce +4 ) via chelation with the directing group controls the regioselectivity of electrophilic nitration without the requirement of additional metal catalyst and external oxidant. Abstract : A new and practical strategy for ceric ammonium nitrate promoted highly chemo‐ and regioselective ortho ‐nitration of aniline carbamates has been developed under mild and neutral conditions without the requirement of additional catalyst and oxidant. Both electron rich and highly electron‐deficient anilines afforded good to excellent yields of the desired products with outstanding functional groups tolerance.