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In situ generation and trapping of aryllithium and arylpotassium species by halogen, sulfur, and carbon electrophiles.

ABSTRACT: A general method has been developed for in situ trapping of arylmetal intermediates by halogen, sulfur, ketone, and aldehyde electrophiles affording the functionalization of the most acidic position in arene. Pentafluorobenzene, benzothiazole, and benzoxazole can be functionalized by using K(3)PO(4) base. For less acidic arenes, tBuOLi base is required. Arenes with DMSO pK(a) values of 35 or less are reactive.

SUBMITTER: Popov I

PROVIDER: S-EPMC2783394 | biostudies-literature | 2009 Nov

REPOSITORIES: biostudies-literature

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In situ generation and trapping of aryllithium and arylpotassium species by halogen, sulfur, and carbon electrophiles.

Popov Ilya I Do Hien-Quang HQ Daugulis Olafs O

The Journal of organic chemistry 20091101 21

A general method has been developed for in situ trapping of arylmetal intermediates by halogen, sulfur, ketone, and aldehyde electrophiles affording the functionalization of the most acidic position in arene. Pentafluorobenzene, benzothiazole, and benzoxazole can be functionalized by using K(3)PO(4) base. For less acidic arenes, tBuOLi base is required. Arenes with DMSO pK(a) values of 35 or less are reactive. ...[more]

PMID: 19827765

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