EFFECTS OF SOLVENT, BASE, AND TEMPERATURE IN THE OPTIMISATION OF A NEW CATALYTIC SYSTEM FOR SONOGASHIRA CROSS-COUPLING USING NCP PINCER PALLADACYCLE

Rosa, Diego S.; Antelo, Francine; Lopes, Toni J.; Moura, Neusa F. de; Rosa, Gilber R.

doi:10.5935/0100-4042.20150045

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Artigo • Quím. Nova 38 (05) • June 2015 • https://doi.org/10.5935/0100-4042.20150045 copy

EFFECTS OF SOLVENT, BASE, AND TEMPERATURE IN THE OPTIMISATION OF A NEW CATALYTIC SYSTEM FOR SONOGASHIRA CROSS-COUPLING USING NCP PINCER PALLADACYCLE

Authorship SCIMAGO INSTITUTIONS RANKINGS

The optimisation of a new catalyst system using NCP pincer palladacycle 1 was investigated using the experimental design technique. NCP pincer palladacycle 1 was previously investigated in Suzuki-Miyaura and Heck-Mizoroki cross-couplings and found to be a highly efficient catalyst precursor. In this study, the effects of the type of base (K₃PO₄ or DABCO), solvent (DMF or dioxane) and reaction temperature (130 or 150 ºC) in the second step on the reactional yield in Sonogashira cross-coupling were assessed using the two-factor design. The results showed that temperature is statistically significant in relation to the reaction yield.

Keywords:
Sonogashira cross-coupling; Dupont’s catalyst; experimental design

	Coded Levels
	-1	+1
Temperature (°C)	130	150
Solvent	Dioxane	DMF
Base	K₃PO₄	DABCO

Essays	Factors
Essays	Temperature (°C)	Solvent	Base
1	-1	-1	-1
2	+1	-1	-1
3	-1	+1	-1
4	+1	+1	-1
5	-1	-1	+1
6	+1	-1	+1
7	-1	+1	+1
8	+1	+1	+1

Entry	Factors			ResponseYield (%)
Entry	Temperature (°C)	Solvent	Base	ResponseYield (%)
1	-1	-1	-1	0
2	+1	-1	-1	30
3	-1	+1	-1	42
4	+1	+1	-1	12
5	-1	-1	+1	8
6	+1	-1	+1	33
7	-1	+1	+1	41
8	+1	+1	+1	5

	Effect	Standard Deviation	Test t Student	Level p	-95% Confidence limit	+95% Confidence limit
Average/Interactions	74.125	0.944	78.545	0.000	71.505	76.745
(A) Temperature (°C)	44.750	1.887	23.709	0.000	39.510	49.990
(B) Solvent	3.750	1.887	1.987	0.118	-1.490	8.990
(C) Base	0.750	1.887	0.397	0.711	-4.490	5.990

		Main effects	p
Yield	Solvent^* * p<0,20 (significant for an 80% confidence level).	-16.5	0.20
	Base	-1.5	0.83

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