Copper‐Catalyzed Cross‐Dehydrogenative Phosphorylation of 2‐Amino‐1, 4‐naphthoquinones with H‐Phosphonates. Issue 41 (4th November 2021)

• Record Type: Journal Article
• Authors: Yang, Fang; Zhou, Qiuju; Wang, Heyan; Tang, Lin
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 41(2022)
• Page Start: 5618
• Page End: 5622
• Publication Date: 2021-11-04
• Subjects: Copper -- Cross-dehydrogenative coupling -- H-phosphonates -- 1, 4-Naphthoquinones -- Phosphorylation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202100870
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: As a simple and efficient system, Cu(OAc)2 ⋅ H2 O and K2 S2 O8 can activate H ‐phosphonates to produce the corresponding dialkyl phosphoryl radicals. The obtained dialkyl phosphoryl radicals react smoothly with 2‐amino‐1, 4‐naphthoquinones, affording accurate preparation of various phosphoryl‐functionalized 2‐amino‐1, 4‐naphthoquinones. The developed copper‐catalyzed cross‐dehydrogenative phosphorylation features broad substrate scope, easily available reagents, high atom economy and operational simplicity, which enables a practical avenue for C−P bond formation. Abstract : An efficient copper‐catalyzed phosphorylation of 2‐amino‐1, 4‐naphthoquinones with H ‐phosphonates via a radical process was developed for the first time. This protocol allows for the synthesis of a variety of phosphoryl‐functionalized 2‐amino 1, 4‐naphthoquinones in moderate to good yields under mild conditions.