Details

Autor(en) / Beteiligte

• Zhang, Jian‐Wu
• Wang, Yuan‐Rui
• Pan, Jia‐Hao
• He, Yi‐Heng
• Yu, Wei
• Han, Bing

Titel

Deconstructive Oxygenation of Unstrained Cycloalkanamines

Ist Teil von

• Angewandte Chemie International Edition, 2020-03, Vol.59 (10), p.3900-3904

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2020

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A deconstructive oxygenation of unstrained primary cycloalkanamines has been developed for the first time using an auto‐oxidative aromatization promoted C(sp3)−C(sp3) bond cleavage strategy. This metal‐free method involves the substitution reaction of cycloalkanamines with hydrazonyl chlorides and subsequent auto‐oxidative annulation to in situ generate pre‐aromatics, followed by N‐radical‐promoted ring‐opening and further oxygenation by 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO) and m‐cholorperoxybenzoic acid (mCPBA). Consequently, a series of 1,2,4‐triazole‐containing acyclic carbonyl compounds were efficiently produced. This protocol features a one‐pot operation, mild reaction conditions, high regioselectivity and ring‐opening efficiency, broad substrate scope, and is compatible with alkaloids, osamines, and peptides, as well as steroids. Opening up: A regioselective deconstructive oxygenation of unstrained cycloalkanamines has been developed for the first time. This metal‐free method involves the substitution reaction of cycloalkanamines with hydrazonyl chlorides and subsequent auto‐oxidative annulation to in situ generate pre‐aromatics, followed by N‐radical‐promoted aromatizative ring‐opening and further oxygenation by (2,2,6,6‐tetramethylpiperidin‐1‐yl)oxyl (TEMPO) and m‐chloroperoxybenzoic acid (mCPBA).