Synthesis of Homoallylic Alcohols in Aqueous Media using Potassium Allyltrifluroborate

Synthesis of Homoallylic Alcohols in Aqueous Media using Potassium Allyltrifluroborate

Barbosa, Fernanda C. G.; Melo, Caio F.; Menezes, Paulo H.; Oliveira, Roberta A.

Abstract:

The addition of crotyl and allylorganometallics to carbonyl compounds is of considerable importance in organic synthesis. However, the utility of many of these organometallics is limited by their susceptibility to air and/or moisture. Organotrifluoroborates have proven to be a good option to replace boronic acids and boronate esters providing advantages over the latter reagents in many types of reactions. Among various allylmetal reagents, potassium allyltrifluoroborate is preferred given the recent demand for safe and sustainable organic synthesis, because this reagent is airstable. As part of ongoing studies on the synthesis and reactivity of organotrifluoroborate salts, herein we report the general and convenient 18-C-6 induced allylation of aldehydes by potassium allyltrifluoroborate.

The addition of crotyl and allylorganometallics to carbonyl compounds is of considerable importance in organic synthesis. However, the utility of many of these organometallics is limited by their susceptibility to air and/or moisture. Organotrifluoroborates have proven to be a good option to replace boronic acids and boronate esters providing advantages over the latter reagents in many types of reactions. Among various allylmetal reagents, potassium allyltrifluoroborate is preferred given the recent demand for safe and sustainable organic synthesis, because this reagent is airstable. As part of ongoing studies on the synthesis and reactivity of organotrifluoroborate salts, herein we report the general and convenient 18-C-6 induced allylation of aldehydes by potassium allyltrifluoroborate.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0217-1

Referências bibliográficas

• [1] 1 (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207–2293; (b) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763–2793.
• [2] 2 Thadani, A. N; Batey, R. A. Org. Lett. 2002, 4, 3827-3830.

Como citar:

Barbosa, Fernanda C. G.; Melo, Caio F.; Menezes, Paulo H.; Oliveira, Roberta A.; "Synthesis of Homoallylic Alcohols in Aqueous Media using Potassium Allyltrifluroborate", p-217-217. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0217-1