Electrochemical Difunctionalization of Terminal Alkynes: Access to 1,4-Dicarbonyl Compounds

2021 ◽  
Author(s):  
Jingcheng Hu ◽  
Li Zeng ◽  
Jiayu Hu ◽  
Rui Ma ◽  
Xue Liu ◽  
...  
Keyword(s):  
Terminal Alkynes ◽  
Dicarbonyl Compounds

Ruthenium-Catalyzed Regioselective Reactions of Nitriles and 1,3-Dicarbonyl Compounds with Terminal Alkynes¹

Synlett ◽  
2009 ◽  
Vol 2009 (20) ◽  
pp. 3355-3359 ◽  
Author(s):  
Shun-Ichi Murahashi ◽  
Takeshi Naota ◽  
Yoshinori Nakano
Keyword(s):  
Terminal Alkynes ◽  
Dicarbonyl Compounds ◽  
Regioselective Reactions

Rhenium- and manganese-catalyzed carbon–carbon bond formation using 1,3-dicarbonyl compounds and alkynes

2010 ◽  
Vol 82 (7) ◽  
pp. 1491-1501 ◽  
Author(s):  
Yoichiro Kuninobu ◽  
Atsushi Kawata ◽  
Salprima S. Yudha ◽  
Hisatsugu Takata ◽  
Mitsumi Nishi ◽  
...  
Keyword(s):  
Molecular Sieves ◽  
Catalytic Amount ◽  
Alder Reaction ◽  
Terminal Alkynes ◽  
Dicarbonyl Compounds ◽  
Keto Esters ◽  
Rhenium Complex ◽  
Diels Alder Reaction ◽  
Carbon Carbon Bond ◽  
Catalyzed Reactions

A rhenium complex, [ReBr(CO)3(thf)]2, catalyzed insertion of terminal alkynes into a C–H bond of active methylene sites of 1,3-dicarbonyl compounds. When a catalytic amount of isocyanide or molecular sieves was added to the reaction mixture, the reaction course changed markedly, and insertion of alkynes into a C–C single bond between α- and β-positions of cyclic and acyclic β-keto esters occurred. The formed acyclic δ-keto esters could be converted to 2-pyranones, which were applied to the synthesis of multisubstituted aromatic compounds via the Diels–Alder reaction and successive elimination of carbon dioxide. In the case of the rhenium-catalyzed reactions between terminal alkynes and β-keto esters without substituent at the α-position, tetrasubstituted benzenes were produced regioselectively by two-to-one reaction of the components. The yields of tetrasubstituted benzenes were improved by using a manganese catalyst.

Mechanistic Study of the Manganese-Catalyzed [2 + 2 + 2] Annulation of 1,3-Dicarbonyl Compounds and Terminal Alkynes

2009 ◽  
Vol 131 (11) ◽  
pp. 4099-4109 ◽  
Author(s):  
Naohiko Yoshikai ◽  
Song-Lin Zhang ◽  
Ken-ichi Yamagata ◽  
Hayato Tsuji ◽  
Eiichi Nakamura
Keyword(s):  
Mechanistic Study ◽  
Terminal Alkynes ◽  
Dicarbonyl Compounds

scholarly journals Addition of 1,3-dicarbonyl compounds to terminal alkynes catalyzed by a cationic cobalt(iii) complex

RSC Advances ◽  
2020 ◽  
Vol 10 (59) ◽  
pp. 36014-36019
Author(s):  
Mohan Chandra Sau ◽  
Manish Bhattacharjee
Keyword(s):  
Terminal Alkynes ◽  
Dicarbonyl Compounds

The Nakamura reaction using the complex, [Cp*Co(CH3CN)3][SbF6]2 as the catalyst has been described. Alkynes on reaction with β-ketoesters afford tetrasubstituted benzenes.

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