Regioselective One‐Pot Synthesis of Triptycenes via Triple‐Cycloadditions of Arynes to Ynolates

• Published in: Angewandte Chemie International Edition Vol. 56; no. 5; pp. 1298 - 1302
• Main Authors: Umezu, Satoshi, dos Passos Gomes, Gabriel, Yoshinaga, Tatsuro, Sakae, Mikei, Matsumoto, Kenji, Iwata, Takayuki, Alabugin, Igor, Shindo, Mitsuru
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 24.01.2017; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Anthracene; aryne; Chelation; Chemistry; Chemistry, Multidisciplinary; directing effect; hyperconjugation; Nucleophiles; Physical Sciences; Regioselectivity; Ring opening; Science & Technology; triptycene; ynolate; KETENE SILYL ACETAL; CASCADE TRANSFORMATIONS; Z-SELECTIVE OLEFINATION; directing effect; CARBONYL-COMPOUNDS; DIECKMANN CONDENSATION; hyperconjugation; RADICAL CASCADES; TRACELESS DIRECTING GROUPS; SUBSTITUENT; aryne; ynolate; STEREOSELECTIVE-SYNTHESIS; triptycene; EFFICIENT

We developed the novel one‐pot synthetic method of substituted triptycenes by the reaction of ynolates and arynes. This four‐step process involves three cycloadditions and electrocyclic ring opening of the strained Dewar anthracene. Each of the three related but structurally distinct classes of nucl...