Literature DB >> 22712572

Copper-catalyzed alkene arylation with diaryliodonium salts.

Robert J Phipps1, Lindsay McMurray, Stefanie Ritter, Hung A Duong, Matthew J Gaunt.   

Abstract

Alkenes and arenes represent two classes of feedstock compounds whose union has fundamental importance to synthetic organic chemistry. We report a new approach to alkene arylation using diaryliodonium salts and Cu catalysis. Using a range of simple alkenes, we have shown that the product outcomes differ significantly from those commonly obtained by the Heck reaction. We have used these insights to develop a number of new tandem and cascade reactions that transform readily available alkenes into complex arylated products that may have broad applications in chemical synthesis.

Entities:  

Mesh:

Substances:

Year:  2012        PMID: 22712572     DOI: 10.1021/ja3039807

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  23 in total

1.  Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

Authors:  Richard P Loach; Owen S Fenton; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2016-01-19       Impact factor: 15.419

2.  Enantioselective α-alkenylation of aldehydes with boronic acids via the synergistic combination of copper(II) and amine catalysis.

Authors:  Jason M Stevens; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2013-08-05       Impact factor: 15.419

3.  Metal-free arylation of ethyl acetoacetate with hypervalent diaryliodonium salts: an immediate access to diverse 3-aryl-4(1H)-quinolones.

Authors:  Andrii Monastyrskyi; Niranjan K Namelikonda; Roman Manetsch
Journal:  J Org Chem       Date:  2015-02-24       Impact factor: 4.354

4.  Transforming Olefins into γ,δ-Unsaturated Nitriles through Copper Catalysis.

Authors:  Xuesong Wu; Jan Riedel; Vy M Dong
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-10       Impact factor: 15.336

5.  Antiproliferative activities of tricyclic amides derived from β-caryophyllene via the Ritter reaction against MDA-MB-231 breast cancer cells.

Authors:  XiXi Xu; Ariane Roseblade; Tristan Rawling; Alison T Ung
Journal:  RSC Med Chem       Date:  2019-12-18

6.  Divergent regioselective Heck-type reaction of unactivated alkenes and N-fluoro-sulfonamides.

Authors:  Chunyang Zhao; Yang Li; Yujiao Dong; Miao Li; Dan Xia; Shuangqiu Gao; Qian Zhang; Qun Liu; Wei Guan; Junkai Fu
Journal:  Nat Commun       Date:  2022-10-22       Impact factor: 17.694

7.  Cu-catalyzed fluorination of diaryliodonium salts with KF.

Authors:  Naoko Ichiishi; Allan J Canty; Brian F Yates; Melanie S Sanford
Journal:  Org Lett       Date:  2013-09-24       Impact factor: 6.005

8.  Copper-catalyzed oxidative Heck reactions between alkyltrifluoroborates and vinyl arenes.

Authors:  Timothy W Liwosz; Sherry R Chemler
Journal:  Org Lett       Date:  2013-06-04       Impact factor: 6.005

9.  Enantioselective functionalization of radical intermediates in redox catalysis: copper-catalyzed asymmetric oxytrifluoromethylation of alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-16       Impact factor: 15.336

10.  Dual visible light photoredox and gold-catalyzed arylative ring expansion.

Authors:  Xing-zhong Shu; Miao Zhang; Ying He; Heinz Frei; F Dean Toste
Journal:  J Am Chem Soc       Date:  2014-04-14       Impact factor: 15.419

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.