Synthesis of N-heterocyclic carbene-palladium-PEPPSI complexes and their catalytic activity in the direct C-H bond activation

Kaloğlu, Nazan; Kaloğlu, Murat; Tahir, Muhammad Nawaz; Arıcı, Cengíz; Bruneau, Christian; Doucet, Henri; Dixneuf, Pierre H.; Çetınkaya, Bekır; Özdemır, İsmaıl

doi:10.1016/j.jorganchem.2017.10.019

Cited by 55 publications

(20 citation statements)

References 55 publications

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“…S3‐S16). Obtained spectroscopic values are consistent with those found in the literature for other benzimidazolium salts 30–32, 41a…”

Section: Resultssupporting

confidence: 89%

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Palladium(II)‐N‐Heterocyclic Carbene Complexes: Efficient Catalysts for the Direct C‐H Bond Arylation of Furans with Aryl Halides

Kaloğlu

Özdemır

2018

Applied Organom Chemis

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This paper contains the synthesis and characterization of the seven new benzimidazolium salts and their corresponding new palladium(II)‐NHC complexes with the general formula [PdX2(NHC)2], (NHC = N‐heterocyclic carbene, X = Cl or Br), and also their catalytic activity in direct C‐H bond arylation of 2‐substituted furan derivatives with aryl bromides and aryl chlorides. Under the optimal conditions, these palladium(II)‐NHC complexes showed the good catalytic performance for the direct C‐H bond arylation of 2‐substituted furans with (hetero)aryl bromides, and with readily available and inexpensive aryl chlorides. The C‐H bond arylation regioselectively produced C5‐arylated furans by using 1 mol% of the palladium(II)‐NHC catalysts in moderate to high yields.

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“…S3‐S16). Obtained spectroscopic values are consistent with those found in the literature for other benzimidazolium salts 30–32, 41a…”

Section: Resultssupporting

confidence: 89%

“…In recent years, a wide variety of studies in this field focused on the developments of new C‐H bond transformations. After this development, various methods for direct arylation of other valuable heteroarenes such as pyrroles, azoles, (benzo)thiophenes and (benzo)furans have been developed …”

Section: Introductionmentioning

confidence: 99%

Palladium(II)‐N‐Heterocyclic Carbene Complexes: Efficient Catalysts for the Direct C‐H Bond Arylation of Furans with Aryl Halides

Kaloğlu

Özdemır

2018

Applied Organom Chemis

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“…[45][46][47][48] In this connection, recently, we have synthesized, characterized, and investigated palladium(II)-N-heterocyclic carbene (Pd-NHC) complexes for catalytic activity in the direct C-H bond activation of different (hetero)aromatic compounds with aryl halides. [49][50][51][52][53][54][55][56][57] The strong σ-donating but poor π-accepting ability of NHC ligands lead to the formation of many stable palladium(II)-NHC complexes. Due to activity, stability and selectivity of palladium(II)-NHC complexes, they have been widely used as highly reactive and rather selective catalysts for numerous direct arylation reactions.…”

Section: Scheme 1 Synthesis Of 2-arylsubstituted Benzoxazoles and Benmentioning

confidence: 99%

“…[58,59] Obtained spectroscopic values for the 1a and 1b compounds are consistent with those found in the literature for benzimidazolium salts. [39,53,[55][56][57]…”

Section: Preparation Of Benzimidazolium Bromidesmentioning

confidence: 99%

Direct C—H Bond Activation of Benzoxazole and Benzothiazole with Aryl Bromides Catalyzed by Palladium(II)‐N‐heterocyclic Carbene Complexes

2018

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Herein, we report that a series of novel palladium(II)‐NHC complexes (NHC=N‐heterocyclic carbene) were synthesized. The structures of all novel complexes were characterized by 1H NMR, 13C NMR, FT‐IR spectroscopy and elemental analysis techniques. These palladium(II)‐NHC complexes were tested as efficient catalysts in the direct C—H bond activation of benzoxazole and benzothiazole with aryl bromides in the presence of 1 mol% catalyst loading at 150 °C for 4 h. Under the given conditions, various aryl bromides were successfully applied as the arylating reagents to achieve the 2‐arylbenzoxazoles and 2‐arylbenzothiazoles in acceptable to high yields.

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“…1 H NMR (500 MHz, CDCl 3 ): δ 8.72 (m, 4H, NC 5 H 5 ), 7.65 (t, 2H, J HH = 7.5 Hz, NC 5 H 5 ), 7.46 (d, 2H, J HH = 7.5 Hz), 7.34 (t, 2H, J HH = 7.5 Hz), 7.27-7.21 (m, 7H), 6.99 (s, 4H), 6.77 (s, 2H), 4.72 (t, 4H, J HH = 6.5 Hz, CH 2 ), 4.07 (s, 2H, CH 2 Ph), 3.58 (t, 4H, J HH = 6.5 Hz, CH 2 ), 2.35(s, 6H, p-CH 3 C 6 H 2 ), 2.22 (s, 12H, o-CH 3 C 6 H 2 ). 13…”

Section: Synthesis Of Pd-peppsi Precatalyst (2a)mentioning

confidence: 99%

Well‐Defined N‐Heterocyclic Carbene‐Palladium Complexes as Efficient Catalysts for Domino Sonogashira Coupling/Cyclization Reaction and C‐H bond Arylation of Benzothiazole

Yadav

Singh

Mishra

et al. 2019

Applied Organom Chemis

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Well‐defined and air‐stable PEPPSI (Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation) themed palladium bis‐N‐heterocyclic carbene complexes have been developed for the domino Sonogashira coupling/cyclization reaction of 2‐iodophenol with a variety of terminal alkynes and C‐H bond arylation of benzothiazole with aryl iodides. The PEPPSI themed palladium complexes, 2a and 2b were synthesized in good yields from the reaction of corresponding imidazolium salts with PdCl2 and K2CO3 in pyridine. The new air‐stable palladium‐NHC complexes were characterized by NMR spectroscopy, X‐ray crystallography, elemental analysis, and mass spectroscopy studies. The PEPPSI themed palladium(II) bis‐N‐heterocyclic carbene complexes 2a and 2b exhibited excellent catalytic activities for domino Sonogashira coupling/cyclization reaction of 2‐iodophenol with terminal alkynes yielding benzofuran derivatives. In addition, the palladium complexes, 2a and 2b successfully catalyzed the direct C‐H bond arylation of benzothiazole with aryl iodides as coupling partners in presence of CuI as co‐catalyst.

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Synthesis of N-heterocyclic carbene-palladium-PEPPSI complexes and their catalytic activity in the direct C-H bond activation

Cited by 55 publications

References 55 publications

Palladium(II)‐N‐Heterocyclic Carbene Complexes: Efficient Catalysts for the Direct C‐H Bond Arylation of Furans with Aryl Halides

Palladium(II)‐N‐Heterocyclic Carbene Complexes: Efficient Catalysts for the Direct C‐H Bond Arylation of Furans with Aryl Halides

Direct C—H Bond Activation of Benzoxazole and Benzothiazole with Aryl Bromides Catalyzed by Palladium(II)‐N‐heterocyclic Carbene Complexes

Well‐Defined N‐Heterocyclic Carbene‐Palladium Complexes as Efficient Catalysts for Domino Sonogashira Coupling/Cyclization Reaction and C‐H bond Arylation of Benzothiazole

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