Arcadi Antonio, Aschi Massimiliano, Chiarini Marco, Fabrizi Giancarlo, Fochetti Andrea, Goggiamani Antonella, Iavarone Federica, Iazzetti Antonia, Serraiocco Andrea, Zoppoli Roberta
Dipartimento di Scienze Fisiche e Chimiche, Università degli Studi di L'Aquila; Via Vetoio, 67100 Coppito, AQ, Italy.
Dipartimento di Bioscienze e Tecnologie Agro-alimentari e Ambientali, Università di Teramo, via R. Balzarini, 1, 64100 Teramo, TE, Italy.
ACS Omega. 2024 Jun 17;9(26):28450-28462. doi: 10.1021/acsomega.4c02409. eCollection 2024 Jul 2.
The palladium-catalyzed reaction of -protected 2-indolylmethyl acetates with soft carbon pronucleophiles is described. Besides the formation of the expected coupling reaction at the C1' position, unprecedented attack at the C3 position of the plausible η-indolyl-palladium intermediate has been observed, and the selectivity control C1'/C3 seems to depend on the nature of the protecting group and ligand. The reactivity of 3-indolylmethyl acetates has also been also investigated. Quantum chemical calculations support the experimental results.
描述了钯催化的受保护的2-吲哚基甲基乙酸酯与软碳亲核前体的反应。除了在C1'位形成预期的偶联反应外，还观察到在可能的η-吲哚基钯中间体的C3位发生了前所未有的进攻，并且C1'/C3的选择性控制似乎取决于保护基团和配体的性质。还研究了3-吲哚基甲基乙酸酯的反应性。量子化学计算支持实验结果。
