Literature DB >> 19373817

Cross dehydrogenative arylation (CDA) of a benzylic C-H bond with arenes by iron catalysis.

Yi-Zhou Li1, Bi-Jie Li, Xing-Yu Lu, Song Lin, Zhang-Jie Shi.   

Abstract

Hooking up: FeCl(2) catalyzes the efficient cross dehydrogenative arylation of substrates having benzylic C-H bonds (see scheme). High regioselectivity was observed during the cross-coupling between compounds containing aromatic C(sp(2))-H bonds and benzylic C(sp(3))-H bonds. This process is proposed to proceed by single-electron-transfer oxidation and Friedel-Crafts alkylation.

Entities:  

Year:  2009        PMID： 19373817     DOI： 10.1002/anie.200900341

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  11 in total

1.  Retention or inversion in stereospecific nickel-catalyzed cross-coupling of benzylic carbamates with arylboronic esters: control of absolute stereochemistry with an achiral catalyst.

Authors:  Michael R Harris; Luke E Hanna; Margaret A Greene; Curtis E Moore; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2013-02-22       Impact factor: 15.419

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.  Synthesis of polyarylated methanes through cross-coupling of tricarbonylchromium-activated benzyllithiums.

Authors:  Genette I McGrew; Jesada Temaismithi; Patrick J Carroll; Patrick J Walsh
Journal:  Angew Chem Int Ed Engl       Date:  2010-07-26       Impact factor: 15.336

4.  Selective synthesis of either enantiomer of an anti-breast cancer agent via a common enantioenriched intermediate.

Authors:  Aaron George Johnson; Marissa M Tranquilli; Michael R Harris; Elizabeth R Jarvo
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

5.  Site-selective coupling of remote C(sp3)-H/meta-C(sp2)-H bonds enabled by Ru/photoredox dual catalysis and mechanistic studies.

Authors:  Hong-Chao Liu; Xiangtao Kong; Xiao-Ping Gong; Yuke Li; Zhi-Jie Niu; Xue-Ya Gou; Xue-Song Li; Yu-Zhao Wang; Wei-Yu Shi; Yan-Chong Huang; Xue-Yuan Liu; Yong-Min Liang
Journal:  Chem Sci       Date:  2022-04-12       Impact factor: 9.969

6.  Evolution of a Strategy for the Enantioselective Total Synthesis of (+)-Psiguadial B.

Authors:  Lauren M Chapman; Jordan C Beck; Caitlin R Lacker; Linglin Wu; Sarah E Reisman
Journal:  J Org Chem       Date:  2018-05-18       Impact factor: 4.354

7.  Oxidative coupling of sp 2 and sp 3 carbon-hydrogen bonds to construct dihydrobenzofurans.

Authors:  Jiang-Ling Shi; Ding Wang; Xi-Sha Zhang; Xiao-Lei Li; Yu-Qin Chen; Yu-Xue Li; Zhang-Jie Shi
Journal:  Nat Commun       Date:  2017-08-10       Impact factor: 14.919

8.  Transition-Metal-Free Synthesis of Polyfunctional Triarylmethanes and 1,1-Diarylalkanes by Sequential Cross-Coupling of Benzal Diacetates with Organozinc Reagents.

Authors:  Baosheng Wei; Qianyi Ren; Thomas Bein; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-17       Impact factor: 15.336

9.  Copper-catalyzed oxidative C(sp3)-H/C(sp2)-H cross-coupling en route to carbocyclic rings.

Authors:  Rui Wang; Yan Li; Ruo-Xing Jin; Xi-Sheng Wang
Journal:  Chem Sci       Date:  2017-03-15       Impact factor: 9.825

Review 10.  Benzylic Methylene Functionalizations of Diarylmethanes.

Authors:  Upma Gulati; Radhika Gandhi; Joydev K Laha
Journal:  Chem Asian J       Date:  2020-09-09
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