Triethyl Phosphite/Benzoyl Peroxide Mediated Reductive Dealkylation of O‐Benzoylhydroxylamines: A Cascade Synthesis of Secondary Amides. Issue 27 (29th June 2020)

• Record Type: Journal Article
• Authors: Aegurla, Balakrishna; Mandle, Ram D.; Shinde, Prasad G.; Parit, Ratan S.; Kamble, Sanjay P.; Sudalai, Arumugam; Senthilkumar, Beeran
• Is Part Of: European journal of organic chemistry. Issue 27(2020)
• Page Start: 4235
• Page End: 4238
• Publication Date: 2020-06-29
• Subjects: O‐Benzoylhydroxylamines -- Amides -- Cascade reactions -- Redox reactions -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000611
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A new triethyl phosphite/benzoyl peroxide (BPO) mediated system has been developed for the synthesis of secondary amides with good to excellent yields in a single step. This unprecedented cascade process involves sequential reduction of N–O bond and benzoylation followed by dealkylation of N–C bond of O ‐benzoylhydroxylamines ( O ‐BHA). The methodology is versatile as it tolerates a variety of aromatic and aliphatic O ‐BHA as substrates to access secondary amides. Abstract : An efficient and operationally simple protocol for the synthesis of 2° amides via reductive benzoylation dealkylation of O ‐benzoylhydroxylamines ( O ‐BHA), by using triethyl phosphite as a reducing agent and benzoyl peroxide as an oxidizing agent is described.