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Microwave assisted Suzuki-Miyaura and Mizoroki-Heck cross-couplings catalyzed by non-symmetric Pd(II) CNS pincers supported by iminophosphorane ligands.

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Title:	Microwave assisted Suzuki-Miyaura and Mizoroki-Heck cross-couplings catalyzed by non-symmetric Pd(II) CNS pincers supported by iminophosphorane ligands.
Authors:	Ramírez-Rave, Sandra¹, Morales-Morales, David², Grévy, Jean-Michel³ jeanmichelg@gmail.com
Source:	Inorganica Chimica Acta. Jun2017, Vol. 462, p249-255. 7p.
Subjects:	Microwave chemistry, Phosphazenes, Ligands (Chemistry), Suzuki reaction, Heck reaction
Abstract:	Two new Pd II non-symmetrical CNS pincer type complexes [PdCl{C 6 H 4 (Ph 2 P = NC 6 H 4 SR- κ 3 -C,N,S)}] [R = Bn ( 3 ) and 4-C 6 H 5 NO 2 ( 4 )], supported by iminophosphorane ligands functionalized with a thioether moiety, were prepared and fully characterized. These compounds and the already known complexes 1 (R = Me) and 2 (R = Ph) were evaluated as catalysts in microwave assisted Suzuki-Miyaura and Mizoroki-Heck coupling reactions. Whereas compound 1 instantaneously decomposed under MW irradiation, as visible black Pd 0 precipitated in both processes, compounds 2 – 4 showed good conversions without apparent decomposition. The coupling reactions were dramatically accelerated under MW radiation when compared to conventional heating, with 3 (R = 4-C 6 H 4 NO 2 ) showing the highest catalytic efficiency of all in both processes. The catalytic activity of complex 2 was further examined in the two cross-couplings with a series of para -substituted bromo-benzenes. Both catalyses proceeded under normal aerobic conditions and were not affected by an excess of elemental Hg. The Mizoroki-Heck reaction operated with high regioselectivity, yielding only the linear 1,2-products. [ABSTRACT FROM AUTHOR]
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Database:	Engineering Source

Description
Abstract:	Two new Pd II non-symmetrical CNS pincer type complexes [PdCl{C 6 H 4 (Ph 2 P = NC 6 H 4 SR- κ 3 -C,N,S)}] [R = Bn ( 3 ) and 4-C 6 H 5 NO 2 ( 4 )], supported by iminophosphorane ligands functionalized with a thioether moiety, were prepared and fully characterized. These compounds and the already known complexes 1 (R = Me) and 2 (R = Ph) were evaluated as catalysts in microwave assisted Suzuki-Miyaura and Mizoroki-Heck coupling reactions. Whereas compound 1 instantaneously decomposed under MW irradiation, as visible black Pd 0 precipitated in both processes, compounds 2 – 4 showed good conversions without apparent decomposition. The coupling reactions were dramatically accelerated under MW radiation when compared to conventional heating, with 3 (R = 4-C 6 H 4 NO 2 ) showing the highest catalytic efficiency of all in both processes. The catalytic activity of complex 2 was further examined in the two cross-couplings with a series of para -substituted bromo-benzenes. Both catalyses proceeded under normal aerobic conditions and were not affected by an excess of elemental Hg. The Mizoroki-Heck reaction operated with high regioselectivity, yielding only the linear 1,2-products. [ABSTRACT FROM AUTHOR]
ISSN:	00201693
DOI:	10.1016/j.ica.2017.03.044