A mild tetradehydro-Diels–Alder reaction of aryldiyne compounds affords exclusively linear products. Issue 15 (29th March 2022)

• Record Type: Journal Article
• Authors: Lu, Yuling; Duan, Xianxian; Chen, Xia; Yao, Meng; Chen, Chunmei; Zhu, Hucheng; Luo, Zengwei; Zhang, Yonghui
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 15(2022)
• Page Start: 3174
• Page End: 3182
• Publication Date: 2022-03-29
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00121g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A mild aromatic tetradehydro-Diels–Alder reaction of aryldiynes is described for linear substituted naphthalenes. Abstract : The thermal tetradehydro-Diels–Alder (TDDA) reaction for the synthesis of polysubstituted aromatic compounds remains underestimated probably due to the harsh conditions and multiproduct results. Herein, a mild intramolecular TDDA reaction of aryldiyne compounds is presented with linear naphthalenes only, exhibiting good functional group tolerance. The reaction is easy to operate and amenable to multigram-scale synthesis. From the preliminary work, it was found that the mild conditions may be the key to the completely linear product in the reactions.