2015
DOI: 10.1007/3418_2015_121
|View full text |Cite
|
Sign up to set email alerts
|

Recent Developments in Pd-Catalyzed Direct Arylations of Heteroarenes with Aryl Halides

Abstract: The direct arylation of heteroaromatic compounds with aryl halides using palladium catalysts has significantly been developed as an effective method for making (hetero)aryl-heteroaryl bonds, which are frequently found in biologically active compounds and functional materials. However, issues regarding costly reagents, regioselectivity, and harsh reaction conditions have to be solved to really compete with the classical transition metal-mediated cross-coupling procedures involving stoichiometric organometallic … Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1

Citation Types

0
8
0

Year Published

2016
2016
2024
2024

Publication Types

Select...
8
1

Relationship

2
7

Authors

Journals

citations
Cited by 15 publications
(8 citation statements)
references
References 53 publications
0
8
0
Order By: Relevance
“…3a,b Apart from aryl halides, benign coupling partners such as boronic acids, sodium sulfinates, acids, silanes, phenylhydrazine hydrate, and [Ph-I-Ph]BF 4 have been used for the synthesis of α-/β-aryl-indoles under palladium-or copper-catalyzed methodologies (eq 1). 3,4 Transition-metal-catalyzed approaches to the direct C-(β)arylation of protected indoles using arenes have also been reported under harsh reaction conditions (eq 2). 5 Nonetheless, these reactions provide a mixture of α-, β-, and α,β-diaryl-indoles and are only suitable for the nonsubstituted and symmetrically substituted arenes, as regioselective coupling of arenes has not been achieved.…”
mentioning
confidence: 99%
“…3a,b Apart from aryl halides, benign coupling partners such as boronic acids, sodium sulfinates, acids, silanes, phenylhydrazine hydrate, and [Ph-I-Ph]BF 4 have been used for the synthesis of α-/β-aryl-indoles under palladium-or copper-catalyzed methodologies (eq 1). 3,4 Transition-metal-catalyzed approaches to the direct C-(β)arylation of protected indoles using arenes have also been reported under harsh reaction conditions (eq 2). 5 Nonetheless, these reactions provide a mixture of α-, β-, and α,β-diaryl-indoles and are only suitable for the nonsubstituted and symmetrically substituted arenes, as regioselective coupling of arenes has not been achieved.…”
mentioning
confidence: 99%
“…ESI-MS m/z 204 [M+H]+. EI-MS, m/z (%): 203 (100), 173 (20), 204 (12), 103 (11), 89 (10). 1 H NMR (400 MHz, CDCl3) δ 8.37 -8.29 (m, 2H), 7.64 -7.59 (m, 2H), 7.57 (d, J = 2.0 Hz, 1H), 6.43 (d, J = 2.0 Hz, 1H), 3.95 (s, 3H).…”
Section: -Methyl-5-(4-nitrophenyl)-1h-pyrazole (3dc)mentioning
confidence: 99%
“…ESI-MS m/z 207 [M+H] + . EI-MS, m/z (%): 206 (100), 176 (26), 148 (20), 133 (27), 89 (53). 1 H NMR (400 MHz, CDCl3) δ 8.88 (s, 1H), 8.33 -8.22 (m, 2H), 8.23 (s, 1H), 7.77 -7.72 (m, 2H).…”
Section: -(4-nitrophenyl)thiazole (3ec)mentioning
confidence: 99%
“…Direct arylation reaction between heteroarenes and aryl halides is a highly desirable strategy for the construction of heterobiaryls because a preliminary organometallic reagent is not necessary, and hence there are fewer reaction steps with a reduction in waste. Typically, a high palladium loading of 2.5–5.0 mol % was required for this catalytic reaction. Previously, we reported PEPPSI-themed PdCl 2 complexes with a NHC ligands ( A2 ), which were effective in direct arylation for the formation of heterobiaryls .…”
Section: Introductionmentioning
confidence: 99%