C−C Bond-Forming Strategy by Manganese-Catalyzed Oxidative Ring-Opening Cyanation and Ethynylation of Cyclobutanol Derivatives

2016 ◽  
Vol 55 (8) ◽  
pp. 2866-2869 ◽  
Author(s):  
Rongguo Ren ◽  
Zhen Wu ◽  
Yan Xu ◽  
Chen Zhu
Keyword(s):  
Ring Opening ◽  
Bond Forming ◽  
Forming Strategy

Bimetallic Radical Redox-Relay Catalysis for the Isomerization of Epoxides to Allylic Alcohols

2019 ◽  
Author(s):  
Ke-Yin Ye ◽  
Terry McCallum ◽  
Song Lin
Keyword(s):  
Ring Opening ◽  
High Reactivity ◽  
Hydrogen Atom Transfer ◽  
Organic Radicals ◽  
Epoxide Ring ◽  
Allylic Alcohols ◽  
Epoxide Ring Opening ◽  
Bond Forming ◽  
Co Catalysts ◽  
The Rich

Organic radicals are generally short-lived intermediates with exceptionally high reactivity. Strategically, achieving synthetically useful transformations mediated by organic radicals requires both efficient initiation and selective termination events. Here, we report a new catalytic strategy, namely bimetallic radical redox-relay, in the regio- and stereoselective rearrangement of epoxides to allylic alcohols. This approach exploits the rich redox chemistry of Ti and Co complexes and merges reductive epoxide ring opening (initiation) with hydrogen atom transfer (termination). Critically, upon effecting key bond-forming and -breaking events, Ti and Co catalysts undergo proton-transfer/electron-transfer with one another to achieve turnover, thus constituting a truly synergistic dual catalytic system.<br>

scholarly journals A unified synthetic strategy to introduce heteroatoms via electrochemical functionalization of alkyl organoboron reagents

2021 ◽  
Author(s):  
Hong Geun Lee ◽  
Taek Dong Chung ◽  
Su Yong Go ◽  
Hyunho Chung ◽  
Samuel Jaeho Shin ◽  
...  
Keyword(s):  
Reaction Kinetics ◽  
Steric Hindrance ◽  
Single Electron ◽  
Electrochemical Studies ◽  
Organoboron Compounds ◽  
Bond Forming ◽  
Unified Protocol ◽  
Synthetic Strategy ◽  
Forming Strategy ◽  
Reaction Profile

Based on systematic electrochemical analyses, an integrated synthetic platform of C(sp3)-based organoboron compounds was established for the introduction of heteroatoms. The electrochemically mediated bond-forming strategy was shown to be highly effective for the functionalization of sp3-hybridized carbon atoms with significant steric hindrance. Moreover, virtually all the nonmetallic heteroatoms could be utilized as reaction partners using one unified protocol. The observed reactivity stems from the two consecutive single-electron oxidations of the substrate, which eventually generates an extremely reactive carbocation as the key intermediate. The detailed reaction profile could be elucidated through multifaceted electrochemical studies and the examination of the reaction kinetics. Ultimately, a new dimension in the activation strategies for organoboron compounds was accomplished through the electrochemically driven reaction development.

scholarly journals Integrative Pericyclic Cascade: An Atom Economic, Multi C−C Bond-Forming Strategy for the Construction of Molecular Complexity

2017 ◽  
Vol 23 (42) ◽  
pp. 10048-10052 ◽  
Author(s):  
David Tejedor ◽  
Samuel Delgado-Hernández ◽  
Jesús Peyrac ◽  
Javier González-Platas ◽  
Fernando García-Tellado
Keyword(s):  
Bond Forming ◽  
Forming Strategy ◽  
Molecular Complexity

Bimetallic Radical Redox-Relay Catalysis for the Isomerization of Epoxides to Allylic Alcohols

2019 ◽  
Author(s):  
Ke-Yin Ye ◽  
Terry McCallum ◽  
Song Lin
Keyword(s):  
Ring Opening ◽  
High Reactivity ◽  
Hydrogen Atom Transfer ◽  
Organic Radicals ◽  
Epoxide Ring ◽  
Allylic Alcohols ◽  
Epoxide Ring Opening ◽  
Bond Forming ◽  
Co Catalysts ◽  
The Rich

Organic radicals are generally short-lived intermediates with exceptionally high reactivity. Strategically, achieving synthetically useful transformations mediated by organic radicals requires both efficient initiation and selective termination events. Here, we report a new catalytic strategy, namely bimetallic radical redox-relay, in the regio- and stereoselective rearrangement of epoxides to allylic alcohols. This approach exploits the rich redox chemistry of Ti and Co complexes and merges reductive epoxide ring opening (initiation) with hydrogen atom transfer (termination). Critically, upon effecting key bond-forming and -breaking events, Ti and Co catalysts undergo proton-transfer/electron-transfer with one another to achieve turnover, thus constituting a truly synergistic dual catalytic system.<br>

scholarly journals Catalyst-controlled regiodivergent ring-opening C(sp3)–Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis

2019 ◽  
Vol 10 (37) ◽  
pp. 8642-8647 ◽  
Author(s):  
Youhei Takeda ◽  
Kaoru Shibuta ◽  
Shohei Aoki ◽  
Norimitsu Tohnai ◽  
Satoshi Minakata
Keyword(s):  
Ring Opening ◽  
Cross Coupling ◽  
Tandem Reaction ◽  
Bond Forming ◽  
Bond Forming Reactions ◽  
Cu Catalyst ◽  
Dual Catalysis

A Pd/Cu catalyst-controlled regiodivergent and stereospecific ring-opening C(sp3)–Si cross-coupling of 2-arylaziridines with silylborane has been developed and a new tandem reaction to give another regioisomer of silylamine has been discovered.

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