ChemInform Abstract: Pd-Catalyzed Cross-Coupling of Terminal Alkynes with Ene-yne-ketones: Access to Conjugated Enynes via Metal Carbene Migratory Insertion.

ChemInform ◽  
2015 ◽  
Vol 46 (48) ◽  
pp. no-no
Author(s):  
Ying Xia ◽  
Zhen Liu ◽  
Rui Ge ◽  
Qing Xiao ◽  
Yan Zhang ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Terminal Alkynes ◽  
Conjugated Enynes ◽  
Migratory Insertion

Pd-catalyzed cross-coupling of terminal alkynes with ene-yne-ketones: access to conjugated enynes via metal carbene migratory insertion

2015 ◽  
Vol 51 (56) ◽  
pp. 11233-11235 ◽  
Author(s):  
Ying Xia ◽  
Zhen Liu ◽  
Rui Ge ◽  
Qing Xiao ◽  
Yan Zhang ◽  
...  
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Terminal Alkynes ◽  
Conjugated Enynes ◽  
Migratory Insertion ◽  
Insertion Process

Pd-catalyzed oxidative cross-coupling of terminal alkynes with ene-yne-ketones has been developed, in which the ene-yne-ketones are served as carbene precursors and metal carbene migratory insertion process is the key step for C–C bond formation.

scholarly journals Selective Manganese-Catalyzed Dimerization and Cross-Coupling of Terminal Alkynes

2021 ◽  
Author(s):  
Stefan Weber ◽  
Luis F. Veiros ◽  
Karl Kirchner
Keyword(s):  
Dft Calculations ◽  
Precious Metal ◽  
Bond Cleavage ◽  
Cross Coupling ◽  
Metal Catalyst ◽  
Catalyst Loading ◽  
Terminal Alkynes ◽  
Migratory Insertion ◽  
Earth Abundant ◽  
First Time

<div>For the first time, an efficient manganese-catalyzed dimerization of terminal alkynes to afford 1,3-enynes is described. This reaction is atom economic, implementing an inexpensive, earth abundant non-precious metal catalyst. The pre-catalyst is the bench-stable alkyl bisphosphine Mn(I) complex fac-[Mn(dippe)(CO)3(CH2CH2CH3)]. The catalytic process is initiated by migratory insertion of a CO ligand into the Mn-alkyl bond to yield an acyl intermediate which undergoes rapid C-H bond cleavage of the alkyne forming an active Mn(I) acetylide catalyst [Mn(dippe)(CO)2(C≡CPh)(η2-HC≡CPh)] together with liberated butanal. A range of aromatic and aliphatic terminal alkynes were efficiently and selectively converted into head-to-head Z-1,3-enynes and head-to-tail gem-1,3-enynes, respectively, in good to excellent yields. Moreover, cross-coupling of aromatic and aliphatic alkynes yields selectively head-to-tail gem-1,3-enynes. In all cases, the reactions were performed at 70 °C with a catalyst loading of 1-2 mol %. A mechanism based on DFT calculations is presented.</div><div><br></div>

scholarly journals Selective Manganese-Catalyzed Dimerization and Cross-Coupling of Terminal Alkynes

2021 ◽  
Author(s):  
Stefan Weber ◽  
Luis F. Veiros ◽  
Karl Kirchner
Keyword(s):  
Dft Calculations ◽  
Precious Metal ◽  
Bond Cleavage ◽  
Cross Coupling ◽  
Metal Catalyst ◽  
Catalyst Loading ◽  
Terminal Alkynes ◽  
Migratory Insertion ◽  
Earth Abundant ◽  
First Time

<div>For the first time, an efficient manganese-catalyzed dimerization of terminal alkynes to afford 1,3-enynes is described. This reaction is atom economic, implementing an inexpensive, earth abundant non-precious metal catalyst. The pre-catalyst is the bench-stable alkyl bisphosphine Mn(I) complex fac-[Mn(dippe)(CO)3(CH2CH2CH3)]. The catalytic process is initiated by migratory insertion of a CO ligand into the Mn-alkyl bond to yield an acyl intermediate which undergoes rapid C-H bond cleavage of the alkyne forming an active Mn(I) acetylide catalyst [Mn(dippe)(CO)2(C≡CPh)(η2-HC≡CPh)] together with liberated butanal. A range of aromatic and aliphatic terminal alkynes were efficiently and selectively converted into head-to-head Z-1,3-enynes and head-to-tail gem-1,3-enynes, respectively, in good to excellent yields. Moreover, cross-coupling of aromatic and aliphatic alkynes yields selectively head-to-tail gem-1,3-enynes. In all cases, the reactions were performed at 70 °C with a catalyst loading of 1-2 mol %. A mechanism based on DFT calculations is presented.</div><div><br></div>

Palladium-Catalyzed Oxidative Cross-Coupling of N-Tosylhydrazones or Diazoesters with Terminal Alkynes: A Route to Conjugated Enynes

2011 ◽  
Vol 123 (15) ◽  
pp. 3572-3576 ◽  
Author(s):  
Lei Zhou ◽  
Fei Ye ◽  
Jiachen Ma ◽  
Yan Zhang ◽  
Jianbo Wang
Keyword(s):  
Cross Coupling ◽  
Terminal Alkynes ◽  
Conjugated Enynes ◽  
Palladium Catalyzed

scholarly journals Atom-Economical Cross-Coupling of Internal and Terminal Alkynes to Access 1,3-Enynes

2021 ◽  
Author(s):  
Mingyu Liu ◽  
Tianhua Tang ◽  
Omar Apolinar ◽  
Rei Matsuura ◽  
Carl A. Busacca ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Terminal Alkynes

scholarly journals ZrCl2(η-C5Me5)2-AlHCl2·(THF)2: efficient hydroalumination of terminal alkynes and cross-coupling of the derived alanes

2013 ◽  
Vol 49 (15) ◽  
pp. 1488 ◽  
Author(s):  
Philip Andrews ◽  
Christopher M. Latham ◽  
Marc Magre ◽  
Darren Willcox ◽  
Simon Woodward
Keyword(s):  
Cross Coupling ◽  
Terminal Alkynes

scholarly journals Iron/copper-catalyzed C–C cross-coupling of aryl iodides with terminal alkynes

2008 ◽  
Vol 49 (41) ◽  
pp. 5961-5964 ◽  
Author(s):  
Chandra M. Rao Volla ◽  
Pierre Vogel
Keyword(s):  
Cross Coupling ◽  
Terminal Alkynes ◽  
Iron Copper ◽  
Aryl Iodides
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