Copper-catalyzed aromatic C–H bond halogenation with lithium halides under aerobic conditions

Mo, Song; Zhu, Yamin; Shen, Zhitao

doi:10.1039/c3ob40185e

Cited by 82 publications

(43 citation statements)

References 53 publications

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“…19 Pyridine derivatives ( 4a – 4s ) were prepared via Suzuki coupling with the corresponding boronic acids and 2-bromopyridines according to the reported procedure. 20 …”

Section: Methodsmentioning

confidence: 99%

Cu-Catalyzed Direct Amidation of Aromatic C–H Bonds: An Access to Arylamines

Qiao

Yang

et al. 2014

J. Org. Chem.

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“…19 Pyridine derivatives ( 4a – 4s ) were prepared via Suzuki coupling with the corresponding boronic acids and 2-bromopyridines according to the reported procedure. 20 …”

Section: Methodsmentioning

confidence: 99%

Cu-Catalyzed Direct Amidation of Aromatic C–H Bonds: An Access to Arylamines

Qiao

Yang

et al. 2014

J. Org. Chem.

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“…Some halogen sources, such as LiCl, NCS, and NIS, also couple with aromatic C-H bonds to form the corresponding C-halogen bonds under appropriate copper catalysis [7,[74][75][76][77][78]. Some representative examples are illustrated in Eqs.…”

Section: Miscellaneous Nucleophilesmentioning

confidence: 99%

Copper-Mediated Intermolecular C–H/C–H and C–H/N–H Couplings via Aromatic C–H Cleavage

Hirano

Miura

2015

Topics in Organometallic Chemistry

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Copper salts and complexes have recently received significant attention as less expensive and abundant alternatives to some noble transition metal catalysts such as palladium, rhodium, and ruthenium, in the research field of C-H activation. They not only replace the above precious metal catalysts in the known C-H transformations but also mediate unique, otherwise challenging, cross-coupling reactions involving C-H bond cleavage. This chapter mainly focuses on recent advances in the copper-mediated or copper-catalyzed intermolecular C-H/C-H and C-H/N-H aromatic couplings. Seminal mechanistic studies on the copper-mediated C-H functionalization are also discussed.

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“…CuCl 2 ‐catalyzed oxychlorination of phenols was reported by Menini and Gusevskaya in which LiCl was used as a chlorinating agent –. Shen and co‐workers reported LiBr/LiCl as a chlorinating agent using Cu(NO 3 ) 2 ⋅ 3 H 2 O as catalyst at 150 °C . Han and co‐workers reported CuI‐mediated halogenation using acetic acid as an additive .…”

Section: Figurementioning

confidence: 99%

Heterogeneous Cu‐MnO Catalyzed Monoselective ortho‐Halogenation of Aromatic C−H Bonds under Visible Light

et al. 2015

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Heterogeneous Cu-MnO-catalyzed selective monohalogenation of aromatic compounds with cheap Nhalosuccinimide (NXS) as ah alogenating agent in the presence of molecular oxygen asanoxidant, under irradiation with visible light is reported. Monochlorination, bromination, and iodinationsw ere achieved in ah ighly selective fashion. Our developed heterogeneous Cu-MnO catalyst without any additive and ligandsw orks well for halogenation with electron-rich substrates and also works selectively with electron poor substrates. Moreover, chlorination occurs efficientlyw itht he more challenging substrates benzoice sters. Theh eterogeneous nature of the reactionwas provenbyh ot filtration test.Aromatic halogenated compounds play av ery important role in synthetic organic chemistry.T hey are widely used as starting materials to build complex molecules via transition-metal-catalyzed cross-couplingr eactions [1] in the synthesis naturalp roducts and important pharmaceutical compounds, including several blockbuster drugs such as Zoloft, Plavix, etc. (Figure 1). [2] The development of efficient and selective methods for their preparation is an important challenge in organic synthesis. Aromatic halides are typicallys ynthesized by direct electrophilic halogenation, [3] directed ortho lithiation, [4] and Sandmeyer reaction. [5] However, these methodsh aved isadvantages such as poor regioselectivitya nd tedious and/or hazardous reaction procedures.Transition-metal-catalyzed direct CÀHf unctionalization with halogenating reagents has been developedi nr ecent years. [6][7][8][9][10][11] Pd-catalyzed directing group assisted CÀHb ond halogenations has attracted considerable attention in recent years.S ignificant advances in this area were reportedb yS anford, Shi, Yu and other groups. [6] To the best of our knowledge, so far few other transition metalsthan Au [7] Rh, [8] Ru, [9] Co [10] and Cu [11] are investigated for direct CÀHh alogenation reaction. Since copper is an economic,a bundant, andv ersatile catalysti th as attracted more attention in direct aryl CÀHh alogenation.Yu and co-workers first reported Cu(OAc) 2 -catalyzedh alogenations of aryl CÀHb onds directed by pyridylg roups using Cl 2 CHCHCl 2 as ac hlorinating agent. [11a] CuCl 2 -catalyzed oxychlorination of phenols was reported by Menini and Gusevskaya in which LiCl was used as ac hlorinating agent. [11b-c] Shen and co-workers reported LiBr/LiCl as ac hlorinating agent using Cu(NO 3 ) 2 ·3H 2 Oa sc atalysta t1 50 8C. [11f] Han and co-workers reported CuI-mediatedh alogenation using acetic acid as an additive. [11h] Halogenation of electron-rich arenes in the presence of CuX 2 /LiX (X = Cl, Br) with acetic acid as as olvent wasr eported by Stahl and co-workers. [11i-j] ortho-Halogenation of benzamides with the removable directing group 2-(pyridine-2-yl)isopropylamine (PIP) was reported by Shi and co-workers. [11k] Electrophilic aromatic halogenation using N-halosuccinimide (NXS) [12] with aBrønsted or Lewis acid or base catalyst is another method to prepare ...

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Copper-catalyzed aromatic C–H bond halogenation with lithium halides under aerobic conditions

Cited by 82 publications

References 53 publications

Cu-Catalyzed Direct Amidation of Aromatic C–H Bonds: An Access to Arylamines

Cu-Catalyzed Direct Amidation of Aromatic C–H Bonds: An Access to Arylamines

Copper-Mediated Intermolecular C–H/C–H and C–H/N–H Couplings via Aromatic C–H Cleavage

Heterogeneous Cu‐MnO Catalyzed Monoselective ortho‐Halogenation of Aromatic C−H Bonds under Visible Light

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