Copper-Catalyzed Annulation Cascades of Alkyne-Tethered α-Bromocarbonyls with Alkynes: An Access to Heteropolycycles

Bang Liu; Jiang-Xi Yu; Yang Li; Jin-Heng Li; De-Liang He

doi:10.1021/acs.orglett.8b00236

Copper-Catalyzed Annulation Cascades of Alkyne-Tethered α-Bromocarbonyls with Alkynes: An Access to Heteropolycycles

Org Lett. 2018 Apr 20;20(8):2129-2132. doi: 10.1021/acs.orglett.8b00236. Epub 2018 Mar 29.

Authors

Bang Liu^{1

2}, Jiang-Xi Yu^{1

2}, Yang Li^{1

2}, Jin-Heng Li^{1

2

3}, De-Liang He¹

Affiliations

¹ State Key Laboratory of Chemo/Biosensing and Chemometrics , Hunan University , Changsha 410082 , China.
² Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle , Nanchang Hangkong University , Nanchang 330063 , China.
³ State Key Laboratory of Applied Organic Chemistry , Lanzhou University , Lanzhou 730000 , China.

PMID: 29595989
DOI: 10.1021/acs.orglett.8b00236

Abstract

We here describe a new Cu-catalyzed annulation cascade of alkyne-tethered α-bromocarbonyls with common alkynes for the synthesis of various heteropolycycle frameworks, including 1 H-benzo[ de]quinolin-2(3 H)-ones, 4 H-dibenzo[ de,g]quinolin-5(6 H)-one, and benzo[ de]chromen-2(3 H)-one, which were constructed with high selectivity. This was achieved by two-component annulation cascades, rather than atom-transfer radical cyclization (ATRC), with alkyne-tethered α-bromocarbonyls for one-step accessing heteropolycycles via C-Br bond split, intramolecular cyclization, intermolecular [4 + 2] annulation, and aryl C(sp²)-H functionalization cascades.

Publication types

Research Support, Non-U.S. Gov't