Pinacol Cross Coupling of 2-[N-(Alkoxycarbonyl)amino] Aldehydes and Aliphatic Aldehydes by [V2Cl3(THF)6]2[Zn2Cl6]. Synthesis of syn,syn-3-[N-(Alkoxycarbonyl)amino] 1,2-Diols

1994 ◽  
Vol 116 (4) ◽  
pp. 1316-1323 ◽  
Author(s):  
Andrei W. Konradi ◽  
Scott J. Kemp ◽  
Steven F. Pedersen
Keyword(s):  
Cross Coupling ◽  
Aliphatic Aldehydes ◽  
Amino Aldehydes

Copper-catalyzed decarboxylative and oxidative decarbonylative cross-coupling between cinnamic acids and aliphatic aldehydes

2018 ◽  
Vol 5 (22) ◽  
pp. 3299-3305 ◽  
Author(s):  
Zaigang Luo ◽  
Xinxin Han ◽  
Yuyu Fang ◽  
Peng Liu ◽  
Chengtao Feng ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Cinnamic Acids ◽  
Aliphatic Aldehydes

A convenient copper-catalyzed decarboxylative and oxidative decarbonylative cross-coupling of cinnamic acids with aliphatic aldehydes was achieved, which provides a useful strategy of C(sp3)–C(sp2) bonds construction for the synthesis of alkyl-substituted E-alkenes.

scholarly journals Nickel-Catalyzed Reductive Coupling of Unactivated Alkyl Bromides and Aliphatic Aldehydes

2021 ◽  
Author(s):  
Cole Cruz ◽  
John Montgomery
Keyword(s):  
Functional Groups ◽  
Catalytic System ◽  
Cross Coupling ◽  
Secondary Alcohols ◽  
Reductive Coupling ◽  
Aliphatic Aldehydes ◽  
Alkyl Bromide ◽  
Alkyl Bromides ◽  
Wide Range ◽  
Ni Species

We report the development of a mild, convenient coupling of aliphatic aldehydes and unactivated alkyl bromides. The catalytic system features the use of a common Ni(II) precatalyst and a readily available bisoxazoline ligand and affords silyl-protected secondary alcohols. The reaction is operationally simple, utilizing Mn as a stoichiometric reductant, and tolerates a wide range of functional groups. Initial mechanistic experiments support a mechanism featuring an alpha-silyloxy Ni species which undergoes formal oxidative addition of the alkyl bromide species via a reductive cross-coupling pathway.

Four-component radical-dual-difunctionalization (RDD) and decarbonylative alkylative peroxidation of two different alkenes with aliphatic aldehydes and TBHP

2019 ◽  
Vol 55 (80) ◽  
pp. 12080-12083 ◽  
Author(s):  
Ren-Xiang Liu ◽  
Feng Zhang ◽  
Yong Peng ◽  
Luo Yang
Keyword(s):  
Alkyl Radical ◽  
Cross Coupling ◽  
Aliphatic Aldehydes

From difunctionalization of a single alkene to radical-dual-difunctionalization of two different alkenes! A alkylative peroxidation and cross-coupling of two alkenes was established with the aliphatic aldehydes as the alkyl radical source.

scholarly journals Nickel-Catalyzed Reductive Coupling of Unactivated Alkyl Bromides and Aliphatic Aldehydes

2021 ◽  
Author(s):  
Cole Cruz ◽  
John Montgomery
Keyword(s):  
Functional Groups ◽  
Catalytic System ◽  
Cross Coupling ◽  
Secondary Alcohols ◽  
Reductive Coupling ◽  
Aliphatic Aldehydes ◽  
Alkyl Bromide ◽  
Alkyl Bromides ◽  
Wide Range ◽  
Ni Species

We report the development of a mild, convenient coupling of aliphatic aldehydes and unactivated alkyl bromides. The catalytic system features the use of a common Ni(II) precatalyst and a readily available bisoxazoline ligand and affords silyl-protected secondary alcohols. The reaction is operationally simple, utilizing Mn as a stoichiometric reductant, and tolerates a wide range of functional groups. Initial mechanistic experiments support a mechanism featuring an alpha-silyloxy Ni species which undergoes formal oxidative addition of the alkyl bromide species via a reductive cross-coupling pathway.

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