One-Pot and Regiospecific Synthesis of 2,3-Disubstituted Indoles from 2-Bromoanilides via Consecutive Palladium-Catalyzed Sonogashira Coupling, Amidopalladation, and Reductive Elimination

2013 ◽  
Vol 78 (9) ◽  
pp. 4558-4562 ◽  
Author(s):  
Bruce Z. Lu ◽  
Han-Xun Wei ◽  
Yongda Zhang ◽  
Wenyi Zhao ◽  
Marine Dufour ◽  
...  
Keyword(s):  
Reductive Elimination ◽  
Sonogashira Coupling ◽  
One Pot ◽  
Palladium Catalyzed

Palladium-Catalyzed Copper-Free Sonogashira Coupling of 2-Bromoarylcarbonyls: Synthesis of Isobenzofurans via One-Pot Reductive Cyclization

Synthesis ◽  
2017 ◽  
Vol 49 (23) ◽  
pp. 5149-5158
Author(s):  
Alavala Krishna Reddy ◽  
Gedu Satyanarayana
Keyword(s):  
Reductive Cyclization ◽  
Sonogashira Coupling ◽  
One Pot ◽  
One Pot Synthesis ◽  
Palladium Catalyzed ◽  
The One

Palladium-catalyzed copper-free Sonogashira coupling of 2-bromocarbonyls is presented. This method afforded the 2-alkynylaryl carbonyls, useful synthons for the accomplishment of many carbocyclic and heterocyclic motifs. Significantly, the strategy was extended to the one-pot synthesis of isobenzofurans via reduction followed by intramolecular 5-exo-dig cyclization.

One‐Pot Palladium‐Catalyzed Carbonylative Sonogashira Coupling using Carbon Dioxide as Carbonyl Source

ChemCatChem ◽  
2021 ◽  
Author(s):  
Huanfeng Jiang ◽  
Wenfang Xiong ◽  
Bowen Wu ◽  
Baiyao Zhu ◽  
Xiaobin Tan ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Sonogashira Coupling ◽  
One Pot ◽  
Palladium Catalyzed

Copper and palladium-catalyzed sequential reactions: one-pot synthesis of isoindolo[2,1-b]isoquinolin-7(5H)-ones

2019 ◽  
Vol 17 (17) ◽  
pp. 4281-4290 ◽  
Author(s):  
Hitesh Kumar Saini ◽  
Shiv Dhiman ◽  
Nitesh Kumar Nandwana ◽  
Rangan Krishnan ◽  
Anil Kumar
Keyword(s):  
Heck Reaction ◽  
Sonogashira Coupling ◽  
One Pot ◽  
Highly Efficient ◽  
One Pot Synthesis ◽  
Ligand Free ◽  
Palladium Catalyzed ◽  
Sequential Reactions

A highly efficient protocol has been developed for the synthesis of diversely substituted isoindolo[2,1-b]isoquinolin-7(5H)-ones through sequential Cu(ii)-catalyzed Sonogashira coupling, intramolecular hydroamidation followed by palladium-catalyzed ligand free Heck reaction.

Synthesis of Internal Alkynes through an Effective Tandem ­Elimination–Hydrodebromination–Cross-Coupling of gem-­Dibromoalkenes with Halobenzenes

Synlett ◽  
2017 ◽  
Vol 29 (02) ◽  
pp. 209-214 ◽  
Author(s):  
Yuan Ji ◽  
Ning Zhong ◽  
Zinan Kang ◽  
Guobing Yan ◽  
Ming Zhao
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Coupling ◽  
Reaction Conditions ◽  
One Pot ◽  
Cross Coupling Reaction ◽  
Sonogashira Coupling Reaction ◽  
Palladium Catalyzed ◽  
Internal Alkyne

Carbon–carbon couplings are among the most important strategies for constructing functional molecules in organic synthetic chemistry, and cheap, diverse, and readily available coupling partners are crucial to these diverse reactions. In this contribution, we report the first palladium-catalyzed C–C cross-coupling reaction of two kinds of organic halide, a gem-dibromoalkene and a halobenzene, as the starting materials. Terminal alkynes were generated in situ through a tandem elimination–hydrodebromination process, and the internal alkyne final products were synthesized in one pot. The reaction proceeded under simple, facile, and classic copper-free Sonogashira coupling reaction conditions in good to excellent yields.

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