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Literature DB >> 25078988

Room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl and heteroaryl bromides.

Feng Gao¹, Byeong-Seon Kim, Patrick J Walsh.

Abstract

An efficient room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl bromides is presented. The Pd(OAc)2/NiXantphos-based catalyst enables the introduction of various aryl and heteroaryl groups, via a deprotonative cross-coupling process (DCCP) in good to excellent yields (60-99%).

Entities: Chemical Disease Gene

Mesh：

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Year: 2014 PMID： 25078988 PMCID： PMC4148349 DOI： 10.1039/c4cc05307a

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

47 in total

1. Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

Authors: Minyan Li; Baris Yücel; Javier Adrio; Ana Bellomo; Patrick J Walsh
Journal: Chem Sci Date: 2014-06-01 Impact factor: 9.825

2. Copper-catalyzed oxidative arylation of heteroarenes under mild conditions using dioxygen as the sole oxidant.

Authors: Fanzhi Yang; Zhaoqing Xu; Zhe Wang; Zhengkun Yu; Rui Wang
Journal: Chemistry Date: 2011-04-27 Impact factor: 5.236

3. Palladium-catalyzed C(sp3)-H arylation of diarylmethanes at room temperature: synthesis of triarylmethanes via deprotonative-cross-coupling processes.

Authors: Jiadi Zhang; Ana Bellomo; Andrea D Creamer; Spencer D Dreher; Patrick J Walsh
Journal: J Am Chem Soc Date: 2012-08-07 Impact factor: 15.419

4. Palladium-catalyzed desulfitative C-arylation of a benzo[d]oxazole C-H bond with arene sulfonyl chlorides.

Authors: Manli Zhang; Shouhui Zhang; Miaochang Liu; Jiang Cheng
Journal: Chem Commun (Camb) Date: 2011-09-23 Impact factor: 6.222

5. Nickel-catalyzed C-H arylation of azoles with haloarenes: scope, mechanism, and applications to the synthesis of bioactive molecules.

Authors: Takuya Yamamoto; Kei Muto; Masato Komiyama; Jérôme Canivet; Junichiro Yamaguchi; Kenichiro Itami
Journal: Chemistry Date: 2011-07-08 Impact factor: 5.236

6. Palladium-catalyzed direct arylation of methyl sulfoxides with aryl halides.

Authors: Tiezheng Jia; Ana Bellomo; Kawtar E L Baina; Spencer D Dreher; Patrick J Walsh
Journal: J Am Chem Soc Date: 2013-02-27 Impact factor: 15.419

7. 2-(2-Arylphenyl)benzoxazole As a Novel Anti-Inflammatory Scaffold: Synthesis and Biological Evaluation.

Authors: Kapileswar Seth; Sanjeev K Garg; Raj Kumar; Priyank Purohit; Vachan S Meena; Rohit Goyal; Uttam C Banerjee; Asit K Chakraborti
Journal: ACS Med Chem Lett Date: 2014-02-17 Impact factor: 4.345

8. Direct multiple C-H bond arylation reaction of heteroarenes catalyzed by cationic palladium complex bearing 1,10-phenanthroline.

Authors: Fumitoshi Shibahara; Eiji Yamaguchi; Toshiaki Murai
Journal: Chem Commun (Camb) Date: 2010-03-05 Impact factor: 6.222

9. Optimization of benzoxazole-based inhibitors of Cryptosporidium parvum inosine 5'-monophosphate dehydrogenase.

Authors: Suresh Kumar Gorla; Mandapati Kavitha; Minjia Zhang; James En Wai Chin; Xiaoping Liu; Boris Striepen; Magdalena Makowska-Grzyska; Youngchang Kim; Andrzej Joachimiak; Lizbeth Hedstrom; Gregory D Cuny
Journal: J Med Chem Date: 2013-05-13 Impact factor: 7.446

8. Copper-catalyzed Direct 2-Arylation of Benzoxazoles and Benzoimidazoles with Aryl Bromides and Cytotoxicity of Products.

Authors: Nan-Nan Jia; Xin-Chuan Tian; Xiao-Xia Qu; Xing-Xiu Chen; Ya-Nan Cao; Yun-Xin Yao; Feng Gao; Xian-Li Zhou
Journal: Sci Rep Date: 2017-03-03 Impact factor: 4.379

8 in total

Room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl and heteroaryl bromides.

1. Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

2. Copper-catalyzed oxidative arylation of heteroarenes under mild conditions using dioxygen as the sole oxidant.

3. Palladium-catalyzed C(sp3)-H arylation of diarylmethanes at room temperature: synthesis of triarylmethanes via deprotonative-cross-coupling processes.

4. Palladium-catalyzed desulfitative C-arylation of a benzo[d]oxazole C-H bond with arene sulfonyl chlorides.

5. Nickel-catalyzed C-H arylation of azoles with haloarenes: scope, mechanism, and applications to the synthesis of bioactive molecules.

6. Palladium-catalyzed direct arylation of methyl sulfoxides with aryl halides.

7. 2-(2-Arylphenyl)benzoxazole As a Novel Anti-Inflammatory Scaffold: Synthesis and Biological Evaluation.

8. Direct multiple C-H bond arylation reaction of heteroarenes catalyzed by cationic palladium complex bearing 1,10-phenanthroline.

9. Optimization of benzoxazole-based inhibitors of Cryptosporidium parvum inosine 5'-monophosphate dehydrogenase.

10. Palladium-catalyzed α-arylation of benzylic phosphonates.

1. Palladium-Catalyzed Selective α-Alkenylation of Pyridylmethyl Ethers with Vinyl Bromides.

2. Palladium-Catalyzed Triarylation of sp³ C-H Bonds in Heteroarylmethanes: Synthesis of Triaryl(heteroaryl)methanes.

3. Palladium-catalyzed C(sp(3))-H Arylation of N-Boc benzylalkylamines via a deprotonative cross-coupling process.

4. Tandem C(sp³)-H Arylation/Oxidation and Arylation/Allylic Substitution of Isoindolinones.

5. Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines.

6. Palladium-Catalyzed Benzylic Arylation of Pyridylmethyl Silyl Ethers: One-Pot Synthesis of Aryl(pyridyl)methanols.

7. Chemoselective Palladium-Catalyzed Deprotonative Arylation/[1,2]-Wittig Rearrangement of Pyridylmethyl Ethers.

8. Copper-catalyzed Direct 2-Arylation of Benzoxazoles and Benzoimidazoles with Aryl Bromides and Cytotoxicity of Products.