TY - JOUR
T1 - New organometallic Schiff-base copper complexes as efficient "click" reaction precatalysts
AU - Liu, Xiang
AU - Novoa, Néstor
AU - MANZUR NAZAL, CECILIA CAROLINA
AU - Carrillo, David
AU - Hamon, Jean René
N1 - Funding Information:
This research has been performed as part of the Chilean-French International Associated Laboratory for "Inorganic Functional Materials" (LIAMIF-CNRS No. 836). Financial support from the China Scholarship Council (CSC) from the People's Republic of China (XL), and the Fondo Nacional de Desarrollo Cient?fico y Tecnol?gico [FONDECYT (Chile), grants no. 1090310 and 1130105 (D. C. and C. M.)], the Vicerrector?a de Investigaci?n y Estudios Avanzados, Pontificia Universidad Cat?lica de Valpara?so, Chile (D. C. and C.M.), the CNRS and the Universit? de Rennes 1 is gratefully acknowledged. N. N. thanks the CONICYT (Chile) and BECAS-CHILE for support of a graduate and Joint Supervision Scholarship (PUCV/UR1).
Publisher Copyright:
© The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016.
Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2016/4/1
Y1 - 2016/4/1
N2 - A new ferrocenyl-containing unsymmetrical CuII-Schiff-base complex, 2, and its covalently poly(methyl) (methacrylate) (PMMA)-grafted counterpart 3 were synthesized and characterized using elemental analysis, electrospray ionisation (ESI) mass spectrometry for 2, and FT-IR spectroscopy. New complex 3 was employed as a precatalyst in the copper-catalyzed [3+2] cycloaddition of organic azides to alkynes (CuAAC, "click" reaction). The active CuI species generated from only 0.2 mol% of CuII precatalyst 2 and sodium ascorbate displayed high activity at room temperature in ethanol for 24 hours allowing the synthesis of a wide variety of 1,4-disubstituted 1,2,3-triazoles in high isolated yields. The PMMA-supported catalyst 3 is also efficient and has been reused at least three times in these "click" reactions without any loss of activity or copper leaching.
AB - A new ferrocenyl-containing unsymmetrical CuII-Schiff-base complex, 2, and its covalently poly(methyl) (methacrylate) (PMMA)-grafted counterpart 3 were synthesized and characterized using elemental analysis, electrospray ionisation (ESI) mass spectrometry for 2, and FT-IR spectroscopy. New complex 3 was employed as a precatalyst in the copper-catalyzed [3+2] cycloaddition of organic azides to alkynes (CuAAC, "click" reaction). The active CuI species generated from only 0.2 mol% of CuII precatalyst 2 and sodium ascorbate displayed high activity at room temperature in ethanol for 24 hours allowing the synthesis of a wide variety of 1,4-disubstituted 1,2,3-triazoles in high isolated yields. The PMMA-supported catalyst 3 is also efficient and has been reused at least three times in these "click" reactions without any loss of activity or copper leaching.
UR - http://www.scopus.com/inward/record.url?scp=84964579545&partnerID=8YFLogxK
U2 - 10.1039/c5nj02681d
DO - 10.1039/c5nj02681d
M3 - Article
AN - SCOPUS:84964579545
VL - 40
SP - 3308
EP - 3313
JO - New Journal of Chemistry
JF - New Journal of Chemistry
SN - 1144-0546
IS - 4
ER -