Synthesis of Biphenyl Tyrosine Via Cross-Coupling Suzuki-Miyaura Reaction Using Aryltrifluoroborate Salts

Author(s)

Vasconcelos, Stanley N. S. ^[1] ; Barbeiro, Cristiane S. ^[1] ; Khan, Amna N. ^[1] ; Stefani, Helio A. ^[1]

Affiliation

^[1] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, BR-05508000 Sao Paulo, SP - Brazil

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 26, n. 4, p. 765-774, APR 2015.
• Web of Science Citations: 4

Abstract

We reported a fast and easy method for obtaining biarylic units from tyrosine derivatives via Suzuki-Miyaura cross-coupling using a variety of substituted and unsubstituted potassium aryl- and heteroaryltrifluoroborate salts. The scope of the methodology was also extended to the formation of bis-tyrosine linked dipeptide bonds, leading to biologically interesting compounds. Some biarylic units were obtained as free amino acids through the one step cleavage reaction in good yields. (AU)

• FAPESP's process: 13/17960-7 - Functionalization of 3-iodo-(L)-Tyrosine via Suzuki-Miyaura Reaction Using Potassium Organotrifluoroborate salts
• Grantee: Stanley Nunes Siqueira Vasconcelos
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 12/00424-2 - Synthesis of small libraries using potassium Organotrifluoroborates in Suzuki-Miyaura reactions
• Grantee: Helio Alexandre Stefani
• Support Opportunities: Research Projects - Thematic Grants