Palladium‐Catalyzed One‐Pot Consecutive Amination and Sonogashira Coupling for Selective Synthesis of 2‐Alkynylanilines

Pan, Shanfei; Ma, Xueji; Zhong, Danni; Chen, Wanzhi; Liu, Miaochang; Wu, Huayue

doi:10.1002/adsc.201500381

Cited by 64 publications

(26 citation statements)

References 75 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The introduction of other groups as well as an amine group was also reported by the Chen, 161 Gu, 162 Chen/Wu, 163 and Lautens 164,165 groups. Selected examples are shown in Scheme 74.…”

Section: Review Syn Thesismentioning

confidence: 61%

Norbornene in Organic Synthesis

Liu

et al. 2018

Synthesis

View full text Add to dashboard Cite

The norbornene skeleton possesses an alkene functionality with a fixed conformation, and represents unique reactivity. The use of norbornene and analogues as substrates is overviewed; reactivities are discussed as well as the role of norbornenes as ligands assisting modern organic transformations.1 Introduction2 Synthesis of Substituted Norbornenes2.1 Preparation of Functionalized Norbornenes by Deprotonation and Substitution Reactions2.2 Preparation of Functionalized Norbornenes under Palladium-Catalyzed Reaction Conditions2.3 Alkylation of Norbornene2.4 Multistep Synthesis3 Synthesis of Substituted Norbornanes3.1 Three-Membered-Ring Formation3.2 Formation of Four-Membered Rings3.3 Five- and Six-Membered Ring Formation3.4 Syntheses of Difunctionalized Norbornanes4 Synthesis of Cyclopentanes4.1 Oxidation Reactions4.2 Ring-Opening Cross Metathesis (ROCM)4.3 Ring-Opening Metathesis Polymerization (ROMP)4.4 Palladium-Catalyzed Ring-Opening of Norbornene5 Norbornene-Mediated Reactions5.1 Palladium Insertion into Carbon–Halide Bonds5.2 Palladium Insertion into N–H and C–H Bonds5.3 Norbornene as Ligand in Mediated Reactions6 Conclusion

show abstract

“…The introduction of other groups as well as an amine group was also reported by the Chen, 161 Gu, 162 Chen/Wu, 163 and Lautens 164,165 groups. Selected examples are shown in Scheme 74.…”

Section: Review Syn Thesismentioning

confidence: 61%

Norbornene in Organic Synthesis

Liu

et al. 2018

Synthesis

View full text Add to dashboard Cite

show abstract

“…We began our study by using homo‐diiodide AA1 , homo‐dialkyne BB1 , and N ‐benzoyloxy morpholine C1 as the model monomer substrates. The conditions originally reported for the ortho amination/ ipso alkynylation reaction, were not suitable for this step‐growth Pd/NBE polymerization as an excess of the alkyne was necessary for high yields. The major side reactions were identified as the direct Sonogashira coupling and ortho amination/ ipso reduction .…”

Section: Figurementioning

confidence: 99%

Modular In Situ Functionalization Strategy: Multicomponent Polymerization by Palladium/Norbornene Cooperative Catalysis

Yoon

Dong

2018

Angew Chem Int Ed

View full text Add to dashboard Cite

Herein, we report a cooperatively palladium/norbornene-catalyzed polymerization, which simplifies the synthesis of functional aromatic polymers, including conjugated polymers. Specifically, an A B C-type multicomponent polymerization that is based on an ortho amination/ipso alkynylation reaction was developed for the preparation of various amine-functionalized arylacetylene-containing polymers. Within a single catalytic cycle, the amine side chains are site-selectively installed in situ by C-H activation during the polymerization process, which represents a major difference from conventional cross-coupling polymerizations. This "in situ functionalization" strategy enables the modular incorporation of functional side chains starting from simple monomers, thereby conveniently affording a diverse range of functional polymers.

show abstract

“…To circumvent the aforementioned problem, the groups of Gu and Chen independently found that, by employing 3‐substituted propiolic acid 13 a or 1,1‐dimethyl‐2‐alkynols 13 b as the masked terminal alkynyl reagents, wherein the terminal alkynes could be gradually released through the loss of carbon dioxide or acetone,, most side reactions could be avoided; thus providing the desired products in good to excellent yields (Scheme ) . The essence of this strategy was the relatively slow in situ generation of terminal alkynes under basic reaction conditions to maintain a low concentration.…”

Section: Monofunctionalized Alkyl Halidesmentioning

confidence: 99%

Alkylating Reagents Employed in Catellani‐Type Reactions

Liu

Gao

Cheng

et al. 2018

Chemistry A European J

View full text Add to dashboard Cite

The Catellani reaction is a powerful strategy that allows the expeditious synthesis of highly substituted arenes, which are not easily accessible through traditional transition-metal-catalyzed cross-coupling reactions. This reaction utilizes the synergistic interplay of palladium and norbornene catalysis to facilitate sequential ortho-C-H functionalization and ipso termination of aryl iodides in a single operation. Since pioneering work by the group of Catellani in 1997, and later by the group of Lautens, this chemistry has attracted considerable attention from the synthetic chemistry community. Dramatic progress has been made by a number of groups in the past two decades. In this Minireview, the alkylating reagents employed in this intriguing reaction and the corresponding applications in organic synthesis are summarized; thus complementing existing reviews to inspire future developments.

show abstract

Palladium‐Catalyzed One‐Pot Consecutive Amination and Sonogashira Coupling for Selective Synthesis of 2‐Alkynylanilines

Cited by 64 publications

References 75 publications

Norbornene in Organic Synthesis

Norbornene in Organic Synthesis

Modular In Situ Functionalization Strategy: Multicomponent Polymerization by Palladium/Norbornene Cooperative Catalysis

Alkylating Reagents Employed in Catellani‐Type Reactions

Contact Info

Product

Resources

About