Electrophilic alkynylation of ketones using hypervalent iodine reagent: a new approach to quaternary carbon formation

Electrophilic alkynylation of ketones using hypervalent iodine reagent: a new approach to quaternary carbon formation

Utaka, Aline; Cavalcanti, Lívia N.; Jr., Luiz F. Silva

Abstract:

Acetylenes have been vastly utilized as intermediates in organic synthesis. Most commonly employed alkynylation method involves the use of nucleophilic alkynylating reagents. However, the use of metal catalysts often leads to undesired homocoupled side product formation diminishing the utility of these protocols. Over the past years, electrophilic alkynylating reagents have emerged as an alternative to the existing methods. Nonetheless, only the α-alkynylation of 1,3-dicarbonyl or carbonyls containing strong α-electron withdrawing groups were described. Herein, we report a new approach for the α-alkynylation of unactivated aromatic ketones using hypervalent iodine reagent.

Acetylenes have been vastly utilized as intermediates in organic synthesis. Most commonly employed alkynylation method involves the use of nucleophilic alkynylating reagents. However, the use of metal catalysts often leads to undesired homocoupled side product formation diminishing the utility of these protocols. Over the past years, electrophilic alkynylating reagents have emerged as an alternative to the existing methods. Nonetheless, only the α-alkynylation of 1,3-dicarbonyl or carbonyls containing strong α-electron withdrawing groups were described. Herein, we report a new approach for the α-alkynylation of unactivated aromatic ketones using hypervalent iodine reagent.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_201391510568

Referências bibliográficas

• [1] 1 Ochiai, M.; Kunishima, M.; Nagao, Y.; Fuji K.; Shiro M. and Fujita, E. J. Am. Chem. Soc., 1986, 108, 8281-8283.
• [2] 2 Waser, J.; Brand, J.P. and González, D.F. Chem. Eur. J. 2010, 16, 9457-9461.

Como citar:

Utaka, Aline; Cavalcanti, Lívia N.; Jr., Luiz F. Silva; "Electrophilic alkynylation of ketones using hypervalent iodine reagent: a new approach to quaternary carbon formation", p-85-85. 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_201391510568