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Fuctionalization of Linear and Angular Phenothiazine and Phenoxazine Ring Systems via Pd(0)/XPhos Mediated Suzuki‐Miyaura Cross‐coupling Reactions
Author(s) -
Onoabedje Efeturi A.,
Okoro Uchechukwu C.,
Knight David W.,
Sarkar Amitabha
Publication year - 2016
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2485
Subject(s) - chemistry , acetonitrile , phenylboronic acid , phenoxazine , phenothiazine , ring (chemistry) , coupling reaction , suzuki reaction , palladium , medicinal chemistry , combinatorial chemistry , catalysis , organic chemistry , medicine , pharmacology
Chloro‐substituted phenothiazines and phenoxazines were successfully derivatized with phenylboronic and styrylboronic acids using Suzuki–Miyaura cross‐coupling reaction catalyzed by Pd(0)/XPhos for the first time in good yields. The protocol employed 4 mol% Pd and 7 mol% XPhos with K 3 PO 4 in acetonitrile at 80°C. The reaction condition is compatible with carbonyl and unprotected N–H groups in substrates. Structural assignments were established by combined spectroscopic (UV, IR, 1 H, and 13 C NMR), MS, and elemental analytical data.