Selective Suzuki- Miyaura Monocouplings with Symmetrical Dibromoarenes and Aryl Ditriflates for the One- Pot Synthesis of Unsymmetrical Triaryls

被引：20

作者：

Minard, Corinne ^{[1
]}

Palacio, Carole ^{[1
]}

Cariou, Kevin ^{[1
]}

Dodd, Robert H. ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, UPR 2301, F-91198 Gif Sur Yvette, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 14期

关键词：

Synthetic methods; C-C coupling; Cross-coupling; Palladium; CROSS-COUPLING REACTIONS; ORGANOBORON COMPOUNDS; MULTIDRUG-RESISTANCE; ARYLBORONIC ACIDS; PALLADIUM CATALYST; P-GLYCOPROTEIN; BORONIC ACIDS; TRIPLE ROLE; NINGALIN-B; DERIVATIVES;

D O I：

10.1002/ejoc.201400090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The various parameters that would permit selective Suzuki-Miyaura monocouplings of symmetrical dihaloarenes were studied. High selectivity and efficiency can be obtained for a broad range of substrates by using operationally simple conditions and widely available reagents. The 38 different examples described provide a valuable toolbox for the rapid access to unsymmetrical triaryls, as illustrated by the preparation of diarylpyridine 8, terphenyl 9, and diarylpyrrole 10.

引用

页码：2942 / 2955

页数：14

共 10 条

[1] One-Pot Synthesis of Unsymmetrical 2,3-Diarylindoles by Site-Selective Suzuki-Miyaura Reactions of N-Methyl-2,3-dibromoindole
Ibad, Muhammad Farooq
Hussain, Munawar
Abid, Obaid-Ur-Rahman
Ali, Asad
Ullah, Ihsan
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Langer, Peter
SYNLETT, 2010, (03) : 411 - 414
[2] Base-Controlled One-Pot Chemoselective Suzuki-Miyaura Reactions for the Synthesis of Unsymmetrical Terphenyls
Li, Xinmin
Feng, Fangfang
Ren, Changyue
Teng, Yong
Hu, Qinghong
Yuan, Zeli
SYNLETT, 2019, 30 (19) : 2131 - 2135
[3] Palladium-Catalyzed Borylation of Aryl Mesylates and Tosylates and Their Applications in One-Pot Sequential Suzuki-Miyaura Biaryl Synthesis
Chow, Wing Kin
So, Chau Ming
Lau, Chak Po
Kwong, Fuk Yee
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (25) : 6913 - 6917
[4] One-pot synthesis of fluorinated terphenyls by site-selective Suzuki-Miyaura reactions of 1,4-dibromo-2-fluorobenzene
Sharif, Muhammad
Zeeshan, Muhammad
Reimann, Sebastian
Villinger, Alexander
Langer, Peter
TETRAHEDRON LETTERS, 2010, 51 (21) : 2810 - 2812
[5] Palladium nanoparticle catalysis: borylation of aryl and benzyl halides and one-pot biaryl synthesis via sequential borylation-Suzuki-Miyaura coupling
Bej, Ansuman
Srimani, Dipankar
Sarkar, Amitabha
GREEN CHEMISTRY, 2012, 14 (03) : 661 - 667
[6] One-Pot Synthesis of Difluorinated ortho-Terphenyls by Site-Selective Suzuki-Miyaura Reactions of 1,2-Dibromo-3,5-difluorobenzene
Sharif, Muhammad
Reimann, Sebastian
Villinger, Alexander
Langer, Peter
SYNLETT, 2010, (06) : 913 - 916
[7] Synthesis of Conjugated Tri(hetero)aryl Derivatives Based on One-Pot Double Suzuki-Miyaura Couplings Using Bifunctional Dipotassium Phenylene-1,4-Bis(Trifluoroborate)
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Petrera, Marilena
Coppi, Donato Ivan
Perna, Filippo Maria
Florio, Saverio
Capriati, Vito
SYNLETT, 2011, (12) : 1761 - 1765
[8] Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids
Mphahlele, Malose Jack
Mphahlele, Mamasegare Mabel
MOLECULES, 2011, 16 (11): : 8958 - 8972
[9] Nano-SiO2: a heterogeneous and reusable catalyst for the one-pot synthesis of symmetrical and unsymmetrical 3,3-di(aryl)indolin-2-ones under solvent-free conditions
Nikoofar, Kobra
Khalili, Zahra
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2016, 71 (01): : 31 - 36
[10] Direct Aldol-Reduction Process using Difluoromethyl Aryl Ketones and Aryl Aldehydes in the Presence of Potassium tert-Butoxide: One-Pot Efficient Stereoselective Synthesis of Symmetrical and Unsymmetrical anti-2,2-Difluoropropane-1,3-diols
Xu, Wei
Medebielle, Maurice
Bellance, Marie-Helene
Dolbier, William R., Jr.
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (16) : 2787 - 2790

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