Development of Unimolecular Tetrakis(piperidin-4-ol) as a Ligand for Suzuki-Miyaura Cross-Coupling Reactions: Synthesis of Incrustoporin and Preclamol

被引：24

作者：

Nallasivam, Jothi L. ^{[1
]}

Fernandes, Rodney A. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 16期

关键词：

Homogeneous catalysis; Palladium; Ligand design; Cross-coupling; Biaryls; Nitrogen heterocycles; PALLADIUM-CATALYZED REACTION; HIGHLY-ACTIVE CATALYST; CARBON BOND FORMATION; ARYL CHLORIDES; SELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; ALLYLIC ALCOHOLS; SCALE SYNTHESIS; C-N; ARYLATION;

D O I：

10.1002/ejoc.201500353

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A domino aza-Cope/aza-Prins cascade enabled the synthesis of a new class of 4-hydroxypiperidine-appended mono, bis, tris, and tetrakis unimolecular compounds that served as efficient ligands to catalyze Suzuki-Miyaura cross-coupling reactions under aerobic conditions. Various biaryls, terphenyls, and heterocyclic biphenyls were obtained in good to excellent yields. The ligands were also capable of catalyzing the Heck-Mizoroki reaction. As an application, the Suzuki-Miyaura coupling reaction was used in the synthesis of incrustoporin, its analogs, and the drug molecule preclamol.

引用

页码：3558 / 3567

页数：10

共 65 条

[1] The discovery of new potent non-peptide Angiotensin II AT1 receptor blockers: A concise synthesis, molecular docking studies and biological evaluation of N-substituted 5-butylimidazole derivatives [J].

Agelis, George ;

Resvani, Amalia ;

Durdagi, Serdar ;

Spyridaki, Katerina ;

Tumova, Tereza ;

Slaninova, Jitina ;

Giannopoulos, Panagiotis ;

Vlahakos, Demetrios ;

Liapakis, George ;

Mavromoustakos, Thomas ;

Matsoukas, John .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 :358-374

[2] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].

Bellina, F ;

Carpita, A ;

Rossi, R .

SYNTHESIS-STUTTGART, 2004, (15) :2419-2440

[3] Synthesis, Structure, Ligand Dynamics, and Catalytic Activity of Cationic [Pd(η3-allyl)(κ2(E,N)-EN-chelate)+ (E = P, O, S, Se) Complexes [J].

Bichler, Bernhard ;

Veiros, Luis F. ;

Oeztopcu, Oezguer ;

Puchberger, Michael ;

Mereiter, Kurt ;

Matsubara, Kouki ;

Kirchner, Karl A. .

ORGANOMETALLICS, 2011, 30 (21) :5928-5942

[4]

Bo Q, 2011, ORG LETT, V13, P2580

[5]

Botella L, 2002, ANGEW CHEM INT EDIT, V41, P179, DOI 10.1002/1521-3773(20020104)41:1<179::AID-ANIE179>3.0.CO

[6]

2-O

[7]

Botella L., 2002, ANGEW CHEMIE, V114, P187

[8] HECK REACTION ON ANTHRAQUINONE DERIVATIVES - LIGAND, SOLVENT, AND SALT EFFECTS [J].

CABRI, W ;

CANDIANI, I ;

DEBERNARDINIS, S ;

FRANCALANCI, F ;

PENCO, S ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5796-5800

[9] An efficient and cost-effective synthesis of 2-phenyl-3-aminopyridine [J].

Caron, S ;

Massett, SS ;

Bogle, DE ;

Castaldi, MJ ;

Braish, TF .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (03) :254-256

[10] PALLADIUM-CATALYZED VINYL SUBSTITUTION-REACTIONS .2. SYNTHESIS OF ARYL SUBSTITUTED ALLYLIC ALCOHOLS, ALDEHYDES, AND KETONES FROM ARYL HALIDES AND UNSATURATED ALCOHOLS [J].

CHALK, AJ ;

MAGENNIS, SA .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (07) :1206-1209

← 1 2 3 4 5 6 7 →