Copper-mediated oxidative homocoupling and rearrangement of N-alkoxyamides: an efficient method for the preparation of aromatic esters. Issue 31 (29th July 2015)

• Record Type: Journal Article
• Authors: Duan, Xiyan; Yang, Kun; Tian, Shuang; Ma, Junying; Li, Yaning; Zou, Jiao; Zhang, Dongliang; Cui, Huanqing
• Is Part Of: Tetrahedron letters. Volume 56:Issue 31(2015)
• Page Start: 4634
• Page End: 4637
• Publication Date: 2015-07-29
• Subjects: BIGQPYZPEWAPBG-UHFFFAOYSA-N -- DDIZAANNODHTRB-UHFFFAOYSA-N -- CPXCDEMFNPKOEF-UHFFFAOYSA-N -- CZNGTXVOZOWWKM-UHFFFAOYSA-N -- LXNFVVDCCWUUKC-UHFFFAOYSA-N -- MSEBQGULDWDIRW-UHFFFAOYSA-N -- PGBFYLVIMDQYMS-UHFFFAOYSA-N -- NGHOLYJTSCBCGC-VAWYXSNFSA-N -- CCRCUPLGCSFEDV-BQYQJAHWSA-N -- AJPPKGMEHMXPMC-UHFFFAOYSA-N -- PQRGTRBYCFLHKY-UHFFFAOYSA-N -- SESFRYSPDFLNCH-UHFFFAOYSA-N -- WVINNNTVGJXIBN-UHFFFAOYSA-N -- VGNDQTDDMDZSAK-UHFFFAOYSA-N -- UKKZHZNQIFTSJN-UHFFFAOYSA-N -- BFJJYXUCGYOXDM-UHFFFAOYSA-N -- CEDBAUKSBZIMJQ-UHFFFAOYSA-N -- QBOVXIMGMVOPQK-UHFFFAOYSA-N; N-Alkoxyamides -- m-CPBA -- Heron rearrangement -- Copper-catalyzed oxidative homocoupling -- Esters; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.06.023
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: N -Alkoxyamides are successfully converted into their corresponding esters in a moderate to satisfactory yields via copper-catalyzed oxidative homocoupling and Heron rearrangement. The process tolerates a wide variety of functional groups and allows the synthesis of sterically hindered ester products not readily accessible by traditional acylation chemistry. A radical-mediated pathway has been tentatively proposed for the oxidative process.