Accessing Lanthanide Diiodide Reactivity for Coupling Alkyl Chlorides to Carbonyl Compounds via the NdI3/Alkali Metal Reduction System

2005 ◽  
Vol 24 (8) ◽  
pp. 1989-1991 ◽  
Author(s):  
William J. Evans ◽  
Penny S. Workman
2004 ◽  
Vol 116 (41) ◽  
pp. 5633-5635 ◽  
Author(s):  
William J. Evans ◽  
David S. Lee ◽  
Charlie Lie ◽  
Joseph W. Ziller

2020 ◽  
Author(s):  
Lucas A. Freeman ◽  
Akachukwu D. Obi ◽  
Haleigh R. Machost ◽  
Andrew Molino ◽  
Asa W. Nichols ◽  
...  

The reduction of the relatively inert carbon–oxygen bonds of CO<sub>2</sub> to access useful CO<sub>2</sub>-derived organic products is one of the most important fundamental challenges in synthetic chemistry. Facilitating this bond-cleavage using earth-abundant, non-toxic main group elements (MGEs) is especially arduous because of the difficulty in achieving strong inner-sphere interactions between CO<sub>2</sub> and the MGE. Herein we report the first successful chemical reduction of CO<sub>2</sub> at room temperature by alkali metals, promoted by a cyclic(alkyl)(amino) carbene (CAAC). One-electron reduction of CAAC-CO<sub>2</sub> adduct (<b>1</b>) with lithium, sodium or potassium metal yields stable monoanionic radicals clusters [M(CAAC–CO<sub>2</sub>)]<sub>n</sub>(M = Li, Na, K, <b> 2</b>-<b>4</b>) and two-electron alkali metal reduction affords open-shell, dianionic clusters of the general formula [M<sub>2</sub>(CAAC–CO<sub>2</sub>)]<sub>n </sub>(<b>5</b>-<b>8</b>). It is notable that these crystalline clusters of reduced CO<sub>2</sub> may also be isolated via the “one-pot” reaction of free CO<sub>2</sub> with free CAAC followed by the addition of alkali metals – a reductive process which does not occur in the absence of carbene. Each of the products <b>2</b>-<b>8</b> were investigated using a combination of experimental and theoretical methods.<br>


Tetrahedron ◽  
1984 ◽  
Vol 40 (10) ◽  
pp. 1701-1711 ◽  
Author(s):  
C. Schnieders ◽  
K. Müllen ◽  
W. Huber
Keyword(s):  

1973 ◽  
Vol 14 (18) ◽  
pp. 1603-1605 ◽  
Author(s):  
Robert L. Shannon ◽  
Richard H. Cox
Keyword(s):  

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