Catalyst‐Controlled Regiodivergent Alkyne Insertion in the Context of C−H Activation and Diels–Alder Reactions: Synthesis of Fused and Bridged Cycles

• Published in: Angewandte Chemie International Edition Vol. 56; no. 28; pp. 8163 - 8167
• Main Authors: Zhou, Xukai, Pan, Yupeng, Li, Xingwei
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 03.07.2017; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Activation; Alkynes; Catalysis; Catalysts; Chemical synthesis; Chemistry; Chemistry, Multidisciplinary; Cobalt; cycloadditions; C−H activation; Diels-Alder reactions; Indoles; Insertion; Physical Sciences; polycycles; Regioselectivity; Rhodium; Science & Technology; Selectivity; ONE-POT SYNTHESIS; ANNULATION; ARENES; TERMINAL ALKYNES; cobalt; cycloadditions; INTERNAL ALKYNES; ARYLATIVE CYCLIZATION; FUNCTIONALIZATION; C-H activation; N-TYPE REACTIONS; INDOLE SYNTHESIS; BOND ACTIVATION; polycycles; rhodium; C−H activation

Rhodium(III)‐ and cobalt(III)‐catalyzed C−H activation of indoles and coupling with 1,6‐enynes is discussed. Under rhodium(III) catalysis, the alkyne insertion follows 2,1‐regioselectivity with a subsequent type‐I intramolecular Diels–Alder reaction (IMDA) to afford [6,5]‐fused cycles. When catalyze...