Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application

被引：7

作者：

Sinai, Adam ^{[1
,2
]}

Simko, Daniel Cs. ^{[2
]}

Szabo, Fruzsina ^{[2
]}

Paczal, Attila ^{[1
]}

Gati, Tamas ^{[1
]}

Benyei, Attila ^{[3
]}

Novak, Zoltan ^{[2
]}

Kotschy, Andras ^{[1
]}

机构：

[1] Servier Res Inst Med Chem, Zahony Utca 7, H-1031 Budapest, Hungary

[2] Eotvos Lorand Univ, Inst Chem, ELTE Lendulet Catalysis & Organ Synth Res Grp, Pazmany Peter Stny 1-A, H-1117 Budapest, Hungary

[3] Univ Debrecen, Dept Pharmaceut Chem, Egyet Ter 1, H-4032 Debrecen, Hungary

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 09期

关键词：

Amination; Cross-coupling; Homogeneous catalysis; Palladium; Phosphine ligands; SUZUKI-MIYAURA; N-TOSYLHYDRAZONES; ROOM-TEMPERATURE; HOMOGENEOUS CATALYSTS; CHLORIDES; SONOGASHIRA; AMINATION; HALIDES; LIBRARIES; ARYLATION;

D O I：

10.1002/ejoc.201901834

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis, temperature-dependent NMR structure investigation and utilization of a new, stable and easily accessible aryl-diadamantylphosphine ligand family is reported. The bulky and electron-rich phosphorus center of the ligand enhances the catalytic activity of palladium in cross-coupling reactions of sterically demanding ortho-substituted aryl halides. In our study, we demonstrated the synthetic applicability of the new phosphine ligands in Buchwald-Hartwig and tosyl hydrazone coupling reactions.

引用

页码：1122 / 1128

页数：7

共 50 条

[21] Palladium-catalyzed cross-coupling reactions with aryl nonaflates:: A practical alternative to aryl triflates
Rottländer, M
Knochel, P
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (01): : 203 - 208
[22] Palladium-Catalyzed Cross-Coupling Reactions with Aryl Nonaflates: A Practical Alternative to Aryl Triflates
J Org Chem, 1 (203):
[23] MECHANISTIC ASPECTS OF AQUEOUS PALLADIUM-CATALYZED ARYL-ARYL CROSS-COUPLING REACTIONS
WALLOW, TI
NOVAK, BM
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 247 - INOR
[24] Palladium-Catalyzed Cross-Coupling Reactions of Cyclopropanols
Rosa, David
Nikolaev, Andrei
Nithiy, Nisha
Orellana, Arturo
SYNLETT, 2015, 26 (04) : 441 - 448
[25] MECHANISM OF PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS
JUTAND, A
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 121 - ORGN
[26] SYNTHESIS OF BETA-ARYL SUBSTITUTED PORPHYRINS BY PALLADIUM-CATALYZED SUZUKI CROSS-COUPLING REACTIONS
CHAN, KS
ZHOU, XA
AU, MT
TAM, CY
TETRAHEDRON, 1995, 51 (11) : 3129 - 3136
[27] Palladium-catalyzed cross-coupling of aryl halides with acylsilanes
Schmink, Jason R.
Krska, Shane W.
Tudge, Matthew T.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
[28] PALLADIUM-CATALYZED CROSS-COUPLING OF VINYLALANES WITH ARYL HALIDES
ALHASSAN, MI
SYNTHETIC COMMUNICATIONS, 1987, 17 (12) : 1413 - 1420
[29] PALLADIUM-CATALYZED CROSS-COUPLING OF ARYL CHLORIDES WITH ARYLSILATRANES
Yamamoto, Yutaro
Baralle, Alexandre
Godefroy, Anais
Murakami, Kei
Yorimitsu, Hideki
Osuka, Atsuhiro
HETEROCYCLES, 2017, 95 (01) : 568 - 574
[30] Palladium-Catalyzed Selective Carboelimination and Cross-Coupling Reactions of Benzocyclobutenols with Aryl Bromides
Chtchemelinine, Andrei
Rosa, David
Orellana, Arturo
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (21): : 9157 - 9162

← 1 2 3 4 5 →