Application of a biarylarsine ligand in Heck and Stille reactions

Application of a biarylarsine ligand in Heck and Stille reactions

Quinteros, Gisela J.; Uberman, Paula M.; Martín, Sandra E.

Abstract:

The Pd coupling reactions are widely used in organic synthesis. Among this group, the Heck reaction occupies a main role in the arylation of alkenes, with wide application in the synthesis of natural products. Moreover, the Stille reaction is a powerful method in organic synthesis due to its broad functional group tolerance and the stability of the reagents. In the last years, developments in coupling reactions are based on designing selective and stable ligands. Although phosphines ligands play a preponderant role in this field, arsines have shown to be excellent supporting ligands, but relatively few have been prepared and applied in catalysis. Recently we have developed a family of biarylarsine ligands that show excellent activity in Stille reaction. Herein we report the evaluation of bulky arsine L1 (Figure 1) in Stille and Heck reactions.

The Pd coupling reactions are widely used in organic synthesis. Among this group, the Heck reaction occupies a main role in the arylation of alkenes, with wide application in the synthesis of natural products. Moreover, the Stille reaction is a powerful method in organic synthesis due to its broad functional group tolerance and the stability of the reagents. In the last years, developments in coupling reactions are based on designing selective and stable ligands. Although phosphines ligands play a preponderant role in this field, arsines have shown to be excellent supporting ligands, but relatively few have been prepared and applied in catalysis. Recently we have developed a family of biarylarsine ligands that show excellent activity in Stille reaction. Herein we report the evaluation of bulky arsine L1 (Figure 1) in Stille and Heck reactions.

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DOI: 10.5151/chempro-15bmos-BMOS2013_201389173721

Referências bibliográficas

• [1] 1 Nadri, S.; Joshaghani, M.; Rafiee, E. App. Cat. A, 2009, 362, 163.
• [2] 2 Naber, J.; Buchwald, S. Adv. Synth. Catal. 2008, 350, 957.
• [3] 3 Baber, R.; Collard, S.; Hooper, M.; Orpen, A.; Pringle, P.; Wilkinson, M.; Wingad, R. Dalton Trans. 2005, 1491.
• [4] 4 Uberman, P.; Lanteri, M.; Parajón Puenzo, S.; Martín, S. Dalton Trans. 2011,40, 9229.

Como citar:

Quinteros, Gisela J.; Uberman, Paula M.; Martín, Sandra E.; "Application of a biarylarsine ligand in Heck and Stille reactions", p-66-66. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201389173721