Synthesis of Tamibarotene via Ullmann-Type Coupling

Bao, Xiaoyi; Qiao, Xue-jun; Bao, Changshun; Liu, Yuting; Zhao, Xuan; Lu, Yi; Chen, Guoliang

doi:10.1021/acs.oprd.7b00089

Cited by 13 publications

(8 citation statements)

References 28 publications

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“…of base in a solvent. According to the literature [30], polar solvents are good choices for Ullmann polymerization in most instances. Thus, dimethyl sulfoxide (DMSO) was first chosen as the solvent for the polymerization at 80 °C (Entry 1).…”

Section: Resultsmentioning

confidence: 99%

Microwave-Assisted Classic Ullmann C–C Coupling Polymerization for Acceptor-Acceptor Homopolymers

Chen

et al. 2019

Polymers

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Developing cheap, clean and atomic-efficient synthetic methodologies for conjugated polymers are always critical for the field of organic electronics. Herein, classic Ullmann coupling polymerization is developed to synthesize a series of Acceptor-Acceptor (A-A) type homopolymers with microwave-assistance, which are supported by nuclear magnetic resonance (NMR), matrix-assisted laser desorption/ionization time of flight mass spectrometry (MALDI-TOF), elemental analysis (EA) and gel permeation chromatography (GPC). The physicochemical properties of these polymers are studied by UV-vis spectroscopy, cyclic voltammetry (CV), thermal gravimetric analysis (TGA), and density functional theory (DFT) calculation. Furthermore, these A-A homopolymers are used as acceptors for all-polymer solar cells (All-PSCs), affording a promising efficiency of 3.08%, which is the highest value for A-A-homopolymer-based organic solar cells.

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Section: Resultsmentioning

confidence: 99%

Microwave-Assisted Classic Ullmann C–C Coupling Polymerization for Acceptor-Acceptor Homopolymers

Chen

et al. 2019

Polymers

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“…Chen et al developed an alternative route via Ullmann coupling to convert aryl bromide 358 to aniline 359 , which was further functionalized to deliver to tamibarotene ( 360 ) (Scheme ). Although the reaction of aryl bromide 358 with aqueous NH 4 OH in the presence of Cu powder or a variety of Cu salts successfully delivered the desired product 359 , it suffered from a high temperature requirement (190 °C) and was thus not desirable for large-scale practice. It was speculated that the poor results were caused by the low solubility of the starting material 358 and that water was unfavorable for the reaction.…”

Section: Applications In Route Design Process Development and Scale-u...mentioning

confidence: 99%

Cu-Mediated Ullmann-Type Cross-Coupling and Industrial Applications in Route Design, Process Development, and Scale-up of Pharmaceutical and Agrochemical Processes

Yang

Zhao

2022

Org. Process Res. Dev.

153

100

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Cu-mediated Ullmann-type cross-coupling has experienced significant advances over the last century since the seminal publication by Ullmann in 1901. These advances have significantly expanded the scope of the original classical Ullmann coupling of aryl halides for formation of diaryl compounds to include the formation of carbon−heteroatom and other carbon− carbon bonds. The introduction of bidentate ligands drastically improved the performance of this class of transformations to enable milder reaction conditions that can tolerate a wide range of sensitive functional groups. Recent development of more powerful second-generation bidentate ligands has further allowed the coupling of less reactive aryl chlorides to proceed smoothly and realized low catalyst and ligand loadings for a broad scope of Ullmann-type cross-coupling reactions. As a result of these breakthrough advances in the past decades, Cu-mediated Ullmann-type cross-coupling reactions have been frequently implemented in academic research and have found ubiquitous industrial applications including the preparation of pharmaceutical and agrochemical products. This review provides an overview of selected general Cu-mediated Ullmann-type transformations for the formation of carbon− carbon and carbon−heteroatom (C−N, C−O, C−S, and C−P) bonds and their applications in route design, process development, and scale-up of pharmaceutical and agrochemical processes.

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“…Next, we tried to associate the unique chelating properties of QCT with the potential benefit of using aqueous ammonia as an environmentally friendly direct nitrogen source to achieve numerous amination reactions (Table 1, entries [18][19][20][21][22][23]. Our investigations commenced with the amination between bromobenzene and aqueaous ammonia using Cu(OAc) 2 •H 2 O and QCT.…”

Section: Letter Syn Lettmentioning

confidence: 99%

“…Tamibarotene, a retinoic acid receptor alpha (RΑR) agonist, was approved in Japan for the treatment of acute promyelocytic leukemia. 19 Chen et al disclosed an effective process for the preparation of tamibarotene, 20 in which the key intermediate 5r could also be prepared with use of the Cu(OAc) 2 •H 2 O and QCT catalytic system, leading to 75% yield. Comparably, this key intermediate was previously prepared through nitrification and reduction, which led to serious pollution with strong acids such as concd H 2 SO 4 and HNO 3 .…”

Section: Letter Syn Lettmentioning

confidence: 99%

Copper(II)-Catalyzed C–N Coupling of Aryl Halides and N-Nucleophiles Promoted by Quebrachitol or Diethylene Glycol

Zhou

et al. 2019

Synlett

Self Cite

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Herein, we report the natural ligand quebrachitol (QCT) as a promoter for a Cu(II) catalyst, which is highly effective for N-arylation of various amines and related aryl halides. A series of diarylamine derivatives were obtained in high yields by using diethylene glycol (DEG) as both ligand and solvent. The C–N coupling reactions proceed under mild conditions and exhibit good functional group tolerance.

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Synthesis of Tamibarotene via Ullmann-Type Coupling

Cited by 13 publications

References 28 publications

Microwave-Assisted Classic Ullmann C–C Coupling Polymerization for Acceptor-Acceptor Homopolymers

Microwave-Assisted Classic Ullmann C–C Coupling Polymerization for Acceptor-Acceptor Homopolymers

Cu-Mediated Ullmann-Type Cross-Coupling and Industrial Applications in Route Design, Process Development, and Scale-up of Pharmaceutical and Agrochemical Processes

Copper(II)-Catalyzed C–N Coupling of Aryl Halides and N-Nucleophiles Promoted by Quebrachitol or Diethylene Glycol

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