Palladium-catalysed three-component coupling reactions of dimethylsilacyclobutane, carbon monoxide and organic halides: a convenient route to cyclic silyl enol ethers

1996 ◽  
pp. 1207 ◽  
Author(s):  
Bhanu P. S. Chauhan ◽  
Yoshifumi Tanaka ◽  
Hiroshi Yamashita ◽  
Masato Tanaka
Keyword(s):  
Carbon Monoxide ◽  
Coupling Reactions ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Organic Halides ◽  
Convenient Route ◽  
Three Component Coupling

Synthesis of Chlorinated Arenes and Hetarenes by One-Pot Cyclizations of 1,3-Bis-silyl Enol Ethers

Synlett ◽  
2019 ◽  
Vol 30 (06) ◽  
pp. 665-673 ◽  
Author(s):  
Peter Langer ◽  
Zahid Hassan
Keyword(s):  
Cost Effective ◽  
Coupling Reactions ◽  
One Pot ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Cross Coupling Reactions ◽  
Silyl Enol Ether ◽  
Synthetic Routes ◽  
Metal Catalyzed ◽  
High Level

This account describes our recent findings and progress in synthesizing chlorinated arenes and hetarenes by one-pot cyclizations of 1,3-bis-silyl enol ether derivatives. These reactions allow for the preparation of highly functionalized products with a high level of regioselectivity. The synthetic routes are cost-effective avoiding additional functionalization steps. The products are difficult to be accessed by other methods. The chlorine atom is of relevance in medicinal and agriculture chemistry. In addition, it allows further functionalizations by transition-metal-catalyzed cross-coupling reactions.1 Introduction2 Cyclizations of 2-Chloro-1,3-bis(silyloxy)-1,3-butadienes2.1 3,5-Dihydroxychlorophthalates2.2 2,4-Dihydroxy-homochlorophthalates2.3 2-(Arylsulfonyl)chloropyridines2.4 1-Azaxanthones3 Cyclizations of 4-Chloro-1,3-bis(trimethylsilyloxy)-1,3-butadienes3.1 3-Chlorosalicylates3.2 Functionalized Chlorobiaryls3.3 3-Chloro-5-(2-chloroethyl)-salicylates3.4 2,4-Dihydroxychlorobenzophenones4 Cyclizations of 2-Chloro-3-(silyloxy)-2-en-1-ones4.1 Functionalized Chlorophenols4.2 Functionalized Chlorinated Biaryls and Chlorofluorenones4.3 Functionalized Chlorochromenones4.4 Functionalized 3-(Methylthio)chlorophenols4.5 Functionalized 3-Chloromethylphenols5 Conclusions6 List of Abbreviations

scholarly journals Radical carbonylations using a continuous microflow system

2009 ◽  
Vol 5 ◽  
Author(s):  
Takahide Fukuyama ◽  
Md Taifur Rahman ◽  
Naoya Kamata ◽  
Ilhyong Ryu
Keyword(s):  
Carbon Monoxide ◽  
Alkyl Halides ◽  
Coupling Reactions ◽  
Tributyltin Hydride ◽  
Microflow Reactor ◽  
Three Component Coupling

Radical-based carbonylation reactions of alkyl halides were conducted in a microflow reactor under pressurized carbon monoxide gas. Good to excellent yields of carbonylated products were obtained via radical formylation, carbonylative cyclization and three-component coupling reactions, using tributyltin hydride or TTMSS as a radical mediator.

Enantioselective Radical Cross-Coupling Reactions of Silyl Enol Ethers Using Chiral Oxovanadium

2001 ◽  
Vol 30 (12) ◽  
pp. 1324-1325 ◽  
Author(s):  
Masaaki Kurihara ◽  
Taeko Hayashi ◽  
Naoki Miyata
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Cross Coupling Reactions
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