期刊
TETRAHEDRON LETTERS
卷 57, 期 25, 页码 2673-2682出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.05.013
关键词
Dehydrogenative C-C coupling; Hypervalent iodine; Pummerer processes; Claisen rearrangement; C-H functionalization; Metal-free cross-coupling
资金
- Fundacio ICIQ MINECO [CTQ2013-46705-R]
- Generalitat de Catalunya [2014 SGR 1192]
- Cellex Foundation through the CELLEX-ICIQ High Throughput Experimentation platform
- Syngenta
- Fundacio ICIQ MINECO (Severo Ochoa Excellence Accreditation) [SEV-2013-0319]
This digest highlights the emergence of the directed metal-free arylation approach employing simple sulfoxide and hypervalent aryliodane. These new processes are characterized by an unusual, and synthetically attractive, retention of the reduced -SR and iodine fragment ortho to the newly formed C-C bond. Although the development of the sulfur- and iodane-based methods have occurred independently, it is becoming increasingly obvious that the two processes are highly analogous in terms of the mechanism and the substrate scope. Indeed, both types of reaction are proposed to occur via a [3,3]-sigmatropic Claisen-type rearrangement, and have been carried out on closely related families of substrates. The digest covers the progress made in 2011-2015 both in the sulfoxide-based methods and in the iodanebased reaction. The ultimate goal is to (a) highlight the synthetic potential of the approach; and (b) offer, for the first time, a unified vision of the two processes. (C) 2016 Elsevier Ltd. All rights reserved.
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