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Synthetic Applications of Pd(II)-catalyzed Carboxylation of Unactivated C-H Bonds

其他書名	Expedient Syntheses of Anthranilic Acids, Oxazinones, and Quinazolinones ; a Thesis Presented
出版	Scripps Research Institute, La Jolla, California, 2010
URL	http://books.google.com.hk/books?id=h406twAACAAJ&hl=&source=gbs_api

註釋Transition metal-catalyzed functionalization of unactivated C-H bonds represents a new synthetic paradigm. Using these bonds directly as functional handles revolutionizes the types of disconnections and strategies synthetic organic chemists have available to them in the construction of complex structures, particularly molecules of medicinal and pharmaceutical importance. The development of a Pd(II)-catalyzed reaction protocol for the direct ortho-carboxylation of anilides to form N-acyl anthranilic acids is discussed. This C-H funtionalization strategy provides a novel and efficient route to biologically relevant heterocycles such as benzoxazinones and quinozolinones, without transient installation of halide functionality. The role of p-toluenesulfonic acid in the activation of C-H bonds is discussed, with mechanistic evidence implicating a p-toluenesulfonate-ligated Pd(II) complex participating in the catalytic cycle.