Metal-Free sp2 and sp3 C-H Functionalization/C-O Bond Forming Reaction

Metal-Free sp2 and sp3 C-H Functionalization/C-O Bond Forming Reaction

Wang, Xueqiang; Donaire, Joan G.; Martin, Ruben

Abstract:

Hypervalent iodine (III) reagents have been employed as mild oxidants in a variety of C-X bondforming reactions. However, superstoichiometric amounts of iodine (III) reagents are typically employed, thus generating equimolar amounts of undesired aryl iodides. In 2005, the Ochiai and Kita groups independently reported a catalytic process involving in situ oxidation of iodoarenes by using meta-chloroperbenzoic acid (m-CPBA). Since then, this concept has been extensively used for the synthesis of a variety of organic molecules. We herein report our preliminary results on an economical approach to benzolactones from simple benzoic acids via metal-free, aryl iodide-catalized C-O bond formation initiated by Csp2-H and Csp3-H functionalization.

Hypervalent iodine (III) reagents have been employed as mild oxidants in a variety of C-X bondforming reactions. However, superstoichiometric amounts of iodine (III) reagents are typically employed, thus generating equimolar amounts of undesired aryl iodides. In 2005, the Ochiai and Kita groups independently reported a catalytic process involving in situ oxidation of iodoarenes by using meta-chloroperbenzoic acid (m-CPBA). Since then, this concept has been extensively used for the synthesis of a variety of organic molecules. We herein report our preliminary results on an economical approach to benzolactones from simple benzoic acids via metal-free, aryl iodide-catalized C-O bond formation initiated by Csp2-H and Csp3-H functionalization.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013815132216

Referências bibliográficas

• [1] 1Ochiai, M.; Takeuchi, Y.; Katayama, T.; Sueda, T.; Miyamoto, K. J. Am.
• [2] Chem. Soc. 2005, 127, 12244.
• [3] 2Dohi, T.; Maruyama, A.; Yoshimura, M.; Morimoto, K.; Tohma, H.; Kita, Y.
• [4] Angew. Chem., Int. Ed. 2005, 44, 6193.
• [5] 3For examples, see: (a) Dohi, T.; Maruyama, A.; Minamitsuji, Y.; Takenaga,
• [6] N.; Kita, Y. Chem. Commun. 2007, 1224. (b) Antonchick, A. P.; Samanta,
• [7] R.; Kulikov, K.; Lategahn, J. Angew. Chem, Int. Ed. 2011, 50, 8605. (c)
• [8] Richardson, R. D.; Wirth, T. Angew. Chem. Int. Ed. 2006, 45, 4402.

Como citar:

Wang, Xueqiang; Donaire, Joan G.; Martin, Ruben; "Metal-Free sp2 and sp3 C-H Functionalization/C-O Bond Forming Reaction", p-155-155. 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_2013815132216