Stepwise approach for sterically hindered Csp3–Csp3 bond formation by dehydrogenative O-alkylation and Lewis acid-catalyzed [1,3]-rearrangement towards the arylalkylcyclopentane skeleton of sesquiterpenes

2020 ◽  
Vol 56 (25) ◽  
pp. 3621-3624
Author(s):  
Ban Fujitani ◽  
Kengo Hanaya ◽  
Takeshi Sugai ◽  
Shuhei Higashibayashi
Keyword(s):  
Lewis Acid ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupling Method ◽  
Stepwise Approach ◽  
Acid Catalyzed ◽  
Sterically Hindered

A stepwise dehydrogenative cross-coupling method was developed for the formation of sterically hindered Csp3–Csp3 bonds.

Ether Synthesis through Reductive Cross-Coupling of Ketones with Alcohols Using Me2SiHCl as both Reductant and Lewis Acid

Synlett ◽  
2017 ◽  
Vol 28 (18) ◽  
pp. 2425-2428 ◽  
Author(s):  
Bill Morandi ◽  
Yong Lee
Keyword(s):  
Functional Groups ◽  
Lewis Acid ◽  
Carbonyl Compounds ◽  
Cross Coupling ◽  
Wide Range ◽  
Direct Cross ◽  
Sterically Hindered ◽  
Polar Functional Groups ◽  
Ether Synthesis ◽  
Dialkyl Ethers

We report that a Lewis acidic silane, Me2SiHCl, can mediate the direct cross-coupling of a wide range of carbonyl compounds with alcohols to form dialkyl ethers. The reaction is operationally simple, tolerates a range of polar functional groups, can be utilized to make sterically hindered ethers, and is extendable to sulfur and nitrogen nucleo­philes.

scholarly journals Lewis acid-mediated Suzuki–Miyaura cross-coupling reaction

2021 ◽  
Vol 4 (12) ◽  
pp. 1080-1088
Author(s):  
Takashi Niwa ◽  
Yuta Uetake ◽  
Motoyuki Isoda ◽  
Tadashi Takimoto ◽  
Miki Nakaoka ◽  
...  
Keyword(s):  
Controlled Release ◽  
Lewis Acid ◽  
Reliable Method ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Carbon Carbon Bond ◽  
Cross Coupling Reaction ◽  
Theoretical Investigations ◽  
Active Intermediate

AbstractThe palladium-catalysed Suzuki–Miyaura cross-coupling reaction of organohalides and organoborons is a reliable method for carbon–carbon bond formation. This reaction involves a base-mediated transmetalation process, but the presence of a base also promotes competitive protodeborylation. Herein, we established a Suzuki–Miyaura cross-coupling reaction via Lewis acid-mediated transmetalation of an organopalladium(II) intermediate with organoborons. Experimental and theoretical investigations indicate that the controlled release of the transmetalation-active intermediate enables base-independent transmetalation under heating conditions and enhances the applicable scope of this process. This system enables us to avoid the addition of a traditional base and, thus, renders substrates with base-sensitive moieties available. Results from this research further expand the overall utility of cross-coupling chemistry.

scholarly journals Lewis Acid Catalyzed Carbonyl–Olefin Metathesis

Synlett ◽  
2017 ◽  
Vol 28 (13) ◽  
pp. 1501-1509 ◽  
Author(s):  
Corinna Schindler ◽  
Jacob Ludwig
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Chemical Biology ◽  
Materials Science ◽  
Bond Formation ◽  
Synthetic Chemistry ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Metathesis Reactions ◽  
Acid Catalyzed

Olefin–olefin metathesis has led to important advances in diverse fields of research, including synthetic chemistry, materials science, and chemical biology. The corresponding carbonyl–olefin metathesis also enables direct carbon–carbon bond formation from readily available precursors, however, currently available synthetic procedures are significantly less advanced. This Synpacts article provides an overview of recent achievements in the field of Lewis acid mediated and Lewis acid catalyzed carbonyl–olefin metathesis reactions.1 Lewis Acid Mediated Carbonyl–Olefin Metathesis2 Lewis Acid Catalyzed Carbonyl–Olefin Metathesis

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