Multicatalytic synthesis of 1,2-dihydroisoquinolin-1-ylphosphonates via a tandem four-component reaction

Zhou, Haibo; Jin, Hua; Ye, Shengqing; He, Xiaodan; Wu, Jie

doi:10.1016/j.tetlet.2009.05.106

Cited by 45 publications

(15 citation statements)

References 100 publications

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“…The 1,2-dihydroisoquinolin-1-ylphosphonates 172 were formed through a one-pot reaction of 2-bromobenzaldehydes 169 , alkynes 170 , amines 171 , and diethyl phosphonate under multicatalytic conditions including palladium and copper salts ( Scheme 37 ) [ 75 ]. This process presumably involves a sequential Sonogashira coupling/cyclization-nucleophilic addition reaction, which is catalyzed by PdCl 2 (PPh 3 ) 2 and CuI whereas Cu(OTf) 2 acts as a Lewis acid.…”

Section: Reviewmentioning

confidence: 99%

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

Haji¹

2016

Beilstein J. Org. Chem.

149

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SummaryMulticomponent reactions (MCRs) are one of the most important processes for the preparation of highly functionalized organic compounds in modern synthetic chemistry. As shown in this review, they play an important role in organophosphorus chemistry where phosphorus reagents are used as substrates for the synthesis of a wide range of phosphorylated heterocycles. In this article, an overview about multicomponent reactions used for the synthesis of heterocyclic compounds bearing a phosphonate group on the ring is given.

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Section: Reviewmentioning

confidence: 99%

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

Haji¹

2016

Beilstein J. Org. Chem.

149

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“…A novel four‐component reaction towards 1,2‐dihydroisoquinolin‐1‐ylphosphonates ( 118 ) has been developed by Wu et al. (Scheme ) 51. Alkynes ( 101 ), amines ( 116 ), diethyl phosphite ( 117 ) and 2‐bromobenzaldehydes ( 115 ) react selectively to form isoquinolines ( 118 ) in high yields.…”

Section: Cross Couplings In Pd‐catalyzed Cascade Reactionsmentioning

confidence: 99%

Recent Advances in Palladium‐Catalyzed Cascade Cyclizations

2011

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The importance of palladium‐catalyzed cross coupling reactions in contemporary organic synthesis is undisputed and underlined by the Nobel Prize for Chemistry in 2010. In addition to the highly efficient cross coupling reactions for single CC bond construction, palladium‐catalyzed cascade processes involving multiple bond formations have emerged in recent years as valuable tools for the rapid synthesis of complex molecular scaffolds. This review presents an overview of the most relevant developments in this field, with a focus on the generation of diverse poly‐ and heterocyclic scaffolds. The generally well understood reactivity of palladium has allowed the discovery of many intriguing novel cascade processes, and the creativity of the synthetic community will undoubtedly lead to many more discoveries in the future.

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“…The resulting iminium was finally trapped by addition of diethylphosphite. Moderate to good yields were obtained depending on the nature of the various components ( Scheme 14 ) [ 13 ].…”

Section: Reviewmentioning

confidence: 99%