Literature DB >> 23339442

Iron-catalyzed allylic arylation of olefins via C(sp3)-H activation under mild conditions.

Masaki Sekine1, Laurean Ilies, Eiichi Nakamura.   

Abstract

An aryl Grignard reagent in the presence of mesityl iodide converts an allylic C-H bond of a cycloalkene or an allylbenzene derivative into a C-C bond in the presence of a catalytic amount of Fe(acac)(3) and a diphosphine ligand at 0 °C. The stereo- and regioselectivity of the reaction, together with deuterium labeling experiments, suggest that C-H bond activation is the slow step in the catalytic cycle preceding the formation of an allyliron intermediate.

Entities:  

Year:  2013        PMID: 23339442     DOI: 10.1021/ol400056z

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 in total

1.  Allylic functionalization of unactivated olefins with Grignard reagents.

Authors:  Hongli Bao; Liela Bayeh; Uttam K Tambar
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-23       Impact factor: 15.336

2.  Nickel or phenanthroline mediated intramolecular arylation of sp3 C-H bonds using aryl halides.

Authors:  William C Wertjes; Lydia C Wolfe; Peter J Waller; Dipannita Kalyani
Journal:  Org Lett       Date:  2013-11-20       Impact factor: 6.005

3.  The direct arylation of allylic sp(3) C-H bonds via organic and photoredox catalysis.

Authors:  James D Cuthbertson; David W C MacMillan
Journal:  Nature       Date:  2015-03-05       Impact factor: 49.962

4.  Mechanistic Study on Allylic Arylation in Water with Linear Polystyrene-Stabilized Pd and PdO Nanoparticles.

Authors:  Atsushi Ohtaka; Misa Kawase; Akira Usami; Shiho Fukui; Mana Yamashita; Kazuki Yamaguchi; Akira Sakon; Tomoya Shiraki; Taiki Ishida; Soma Nagata; Yuji Kimura; Go Hamasaka; Yasuhiro Uozumi; Tsutomu Shinagawa; Osamu Shimomura; Ryôki Nomura
Journal:  ACS Omega       Date:  2019-09-13

5.  Metal-free allylic C-H nitrogenation, oxygenation, and carbonation of alkenes by thianthrenation.

Authors:  Ming-Shang Liu; Hai-Wu Du; Wei Shu
Journal:  Chem Sci       Date:  2021-12-20       Impact factor: 9.825

6.  Iron-catalyzed α-C-H functionalization of π-bonds: cross-dehydrogenative coupling and mechanistic insights.

Authors:  Yidong Wang; Jin Zhu; Rui Guo; Haley Lindberg; Yi-Ming Wang
Journal:  Chem Sci       Date:  2020-10-16       Impact factor: 9.825

Review 7.  Iron-catalyzed domino coupling reactions of π-systems.

Authors:  Austin Pounder; William Tam
Journal:  Beilstein J Org Chem       Date:  2021-12-07       Impact factor: 2.883

  7 in total

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