scholarly journals Synthesis of α- and β-Carbolines by a Metalation/Negishi Cross-Coupling/SNAr Reaction Sequence

2021 ◽  
Author(s):  
Stefan Roesner ◽  
Shainthavaan Sathiyalingam
Keyword(s):  
Cross Coupling ◽  
Reaction Sequence ◽  
Snar Reaction

scholarly journals Synthesis of α- and β-Carbolines by a Metalation/Negishi Cross-Coupling/SNAr Reaction Sequence

2021 ◽  
Author(s):  
Shainthavaan Sathiyalingam ◽  
Stefan Roesner
Keyword(s):  
Efficient Method ◽  
Continuous Flow ◽  
Medicinal Chemistry ◽  
Cross Coupling ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Reaction Sequence ◽  
Snar Reaction ◽  
Privileged Scaffolds

Carbolines are considered to be privileged scaffolds in medicinal chemistry. An efficient method for the synthesis of α- and β-carbolines from fluoropyridines and 2-haloanilines is reported. This streamlined procedure consists of a four-step directed ortho-lithiation, zincation, Negishi cross-coupling, and intramolecular nucleophilic aromatic substitution, providing access to a diverse set of functionalized carbolines. While the procedure is applicable to batch conditions, the generation of arylzinc intermediates in continuous flow has been demonstrated.

Towards the Total Synthesis of Schisandrene: Stereoselective Synthesis of the Dibenzocyclooctadiene Lignan Core

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 908-911 ◽  
Author(s):  
K. Babu ◽  
Arramshetti Venkanna ◽  
Borra Poornima ◽  
Bandi Siva ◽  
B. Babu
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Asymmetric Reduction ◽  
Cross Coupling ◽  
Membered Ring ◽  
Stille Reaction ◽  
Reaction Sequence ◽  
Ring Closing Metathesis ◽  
Synthetic Strategy ◽  
First Time

A stereoselective synthesis of the dibenzocyclooctadiene ­lignan core of the natural product schisandrene is described. Starting from readily available gallic acid, the synthetic strategy involves Suzuki–Miyaura cross-coupling, Stille reaction, and ring-closing metathesis (RCM) in the reaction sequence. The required asymmetric center at C-7′ was established by an asymmetric reduction of a keto compound using the Corey–Bakshi–Shibata (CBS) catalyst. In our approach, the eight-membered ring was achieved by RCM for the first time.

Sequential O-Arylation/Lanthanide(III)-Catalyzed [3,3]-Sigmatropic Rearrangement of Bromo-Substituted Allylic Alcohols

Synlett ◽  
2017 ◽  
Vol 28 (20) ◽  
pp. 2865-2870 ◽  
Author(s):  
Timothy Ramadhar ◽  
Jun-ichi Kawakami ◽  
Robert Batey
Keyword(s):  
Claisen Rearrangement ◽  
Cross Coupling ◽  
Sigmatropic Rearrangement ◽  
Mitsunobu Reaction ◽  
Allylic Alcohols ◽  
Aryl Ether ◽  
Claisen Rearrangements ◽  
Snar Reaction ◽  
Aryl Ethers

Lanthanide(III)-catalyzed aryl-Claisen rearrangement of substrates bearing halo-substituted allyl groups, specifically 2-bromoallyl aryl ethers, afford ortho-2-bromoallylphenols. Aryl ether substrates were synthesized from brominated allylic alcohols via Mitsunobu reaction, Cu(II)-catalyzed arylation using potassium aryltrifluoroborate salts, or SNAr reaction. Aryl-Claisen rearrangements proceeded in moderate to excellent yields using Eu(III) catalysis. The alkenylbromide functionality remains intact, illustrating the compatibility of synthetically important alkenylhalides during C–O/C–C σ-bond migration processes. Subsequent derivatization of the ortho-2-bromoallylphenol products through O-alkylation or C-arylation/alkenylation via Suzuki–Miyaura cross-coupling demonstrate the potential to access densely-functionalized molecules.

One-pot Synthesis of Dibenzofurans via SNAr and Subsequent Ligand-free Palladium-catalyzed Intramolecular Aryl-aryl Cross-coupling Reactions under Microwave Irradiation

2011 ◽  
Vol 66 (8) ◽  
pp. 833-836
Author(s):  
Zhiping Che ◽  
Hui Xu
Keyword(s):  
Microwave Irradiation ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Cross Coupling Reactions ◽  
Ligand Free ◽  
Palladium Catalyzed ◽  
Snar Reaction

An efficient one-pot synthesis of dibenzofurans, via SNAr reaction of aryl halides and ortho-bromophenols in the presence of anhydrous K2CO3 and subsequent ligand-free palladium-catalyzed intramolecular aryl-aryl cross-coupling cyclization under microwave irradiation, is described.

ChemInform Abstract: One-Pot Synthesis of 1-Arylmethyl-4-[(E)-alk-1-enyl]-1H-1,2,3-triazoles via a Cross-Coupling/Click Reaction Sequence.

ChemInform ◽  
2014 ◽  
Vol 45 (36) ◽  
pp. no-no
Author(s):  
Masayuki Hoshi ◽  
Mitsuhiro Okimoto ◽  
Asuka Oikawa ◽  
Shunsuke Miyawaki ◽  
Yasutaka Shimotori
Keyword(s):  
Click Reaction ◽  
Cross Coupling ◽  
Reaction Sequence ◽  
One Pot ◽  
One Pot Synthesis

Synthesis of 2,3′-spirobi[indolin]-2-ones enabled by a tandem nucleophilic benzylation/C(sp2)–N cross-coupling reaction sequence

2017 ◽  
Vol 15 (28) ◽  
pp. 5887-5892 ◽  
Author(s):  
Baodong Cui ◽  
Jing Shan ◽  
Changlun Yuan ◽  
Wenyong Han ◽  
Nanwei Wan ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Reaction Sequence ◽  
Efficient Strategy ◽  
Cross Coupling Reaction ◽  
New Perspective

This study provides an efficient strategy for the construction of spiro[pyrrolidin-3,2′-oxindoles] and represents a new perspective for the synthesis of spirocyclic oxindoles.

One-pot synthesis of 1-arylmethyl-4-[(E)-alk-1-enyl]-1H-1,2,3-triazoles via a cross-coupling/click reaction sequence

RSC Advances ◽  
2014 ◽  
Vol 4 (5) ◽  
pp. 2124-2128 ◽  
Author(s):  
Masayuki Hoshi ◽  
Mitsuhiro Okimoto ◽  
Asuka Oikawa ◽  
Shunsuke Miyawaki ◽  
Yasutaka Shimotori
Keyword(s):  
Click Reaction ◽  
Cross Coupling ◽  
Reaction Sequence ◽  
One Pot ◽  
One Pot Synthesis
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