Gold-catalyzed cascade cyclization of N-propargyl ynamides: rapid access to functionalized indeno[1,2-c]pyrroles

2018 ◽  
Vol 5 (16) ◽  
pp. 2468-2472 ◽  
Author(s):  
Wen-Bo Shen ◽  
Bo Zhou ◽  
Zhi-Xin Zhang ◽  
Han Yuan ◽  
Wei Fang ◽  
...  
Keyword(s):  
Cascade Cyclization ◽  
Rapid Access ◽  
Vinyl Cation ◽  
Practical Synthesis

A new gold-catalyzed cascade cyclization of N-propargyl ynamides involving a presumable vinyl cation intermediate has been developed, allowing the efficient and practical synthesis of various functionalized indeno[1,2-c]pyrroles.

Cascade cyclization and acyl migration of propargylic esters with isocyanides: rapid access to substituted furans

2019 ◽  
Vol 55 (58) ◽  
pp. 8394-8397 ◽  
Author(s):  
Jie Hu ◽  
Youwen Fei ◽  
Hongbin Zhao ◽  
Zhishuang Wang ◽  
Chunju Li ◽  
...  
Keyword(s):  
Acyl Migration ◽  
Furan Derivatives ◽  
Cascade Cyclization ◽  
Rapid Access ◽  
Propargylic Esters ◽  
Substituted Furans

A novel rearrangement of ester-activated propargylic acetate with isocyanide has been disclosed. This protocol enables a quick synthesis of polysubstituted furan derivatives.

ChemInform Abstract: Rapid Access to 3-(Aminomethyl)isoquinoline-Fused Polycyclic Compounds by Copper-Catalyzed Four-Component Coupling, Cascade Cyclization, and Oxidation.

ChemInform ◽  
2010 ◽  
Vol 41 (2) ◽  
Author(s):  
Yusuke Ohta ◽  
Yushi Kubota ◽  
Tsuyoshi Watabe ◽  
Hiroaki Chiba ◽  
Shinya Oishi ◽  
...  
Keyword(s):  
Polycyclic Compounds ◽  
Cascade Cyclization ◽  
Rapid Access

Rapid Access to 3-(Aminomethyl)isoquinoline-Fused Polycyclic Compounds by Copper-Catalyzed Four-Component Coupling, Cascade Cyclization, and Oxidation

2009 ◽  
Vol 74 (16) ◽  
pp. 6299-6302 ◽  
Author(s):  
Yusuke Ohta ◽  
Yushi Kubota ◽  
Tsuyoshi Watabe ◽  
Hiroaki Chiba ◽  
Shinya Oishi ◽  
...  
Keyword(s):  
Polycyclic Compounds ◽  
Cascade Cyclization ◽  
Rapid Access

Stereodivergent Alkyne Hydrofluorination Using a Simple Practical Reagent

2020 ◽  
Author(s):  
Rui Guo ◽  
Xiaotian Qi ◽  
Hengye Xiang ◽  
Paul Geaneoates ◽  
Ruihan Wang ◽  
...  
Keyword(s):  
Bond Formation ◽  
Biologically Active ◽  
Dft Studies ◽  
Thermodynamic Control ◽  
Important Goal ◽  
Peptide Bonds ◽  
Metal Free ◽  
Vinyl Cation ◽  
E And Z Isomers ◽  
Vinyl Fluorides

Vinyl fluorides play an important role in drug development as they serve as bioisosteres for peptide bonds and are found in a range of biologically active molecules. The discovery of safe, general and practical procedures to prepare vinyl fluorides remains an important goal and challenge for synthetic chemistry. Here we introduce an inexpensive and easily-handled reagent and report simple, scalable, and metal-free protocols for the regioselective and stereodivergent hydrofluorination of alkynes to access both the E and Z isomers of vinyl fluorides. These conditions were suitable for a diverse collection of alkynes, including several highly-functionalized pharmaceutical derivatives. Mechanistic and DFT studies support C–F bond formation through a vinyl cation intermediate, with the (E)- and (Z)-hydrofluorination products forming under kinetic and thermodynamic control, respectively.<br>

Fe-Catalyzed Conjunctive Cross-Couplings of Unactivated Alkenes with Grignard Reagents

2020 ◽  
Author(s):  
Lei Liu ◽  
Wes Lee ◽  
Cassandra R. Youshaw ◽  
Mingbin Yuan ◽  
Michael B. Geherty ◽  
...  
Keyword(s):  
Functional Groups ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Turnover Frequency ◽  
Diverse Range ◽  
Cascade Cyclization ◽  
Radical Cascade

The first iron-catalyzed three-component cross-coupling of unactivated olefins with alkyl halides and Grignard reagents is reported. The reaction operates under fast turnover frequency and tolerates a diverse range of sp2-hybridized nucleophiles, alkyl halides, and unactivated olefins bearing diverse functional groups to yield the desired 1,2-alkylarylated products with high regiocontrol. Further, we demonstrate that this protocol is amenable for the synthesis of new (hetero)carbocycles including tetrahydrofurans and pyrrolidines via a three-component radical cascade cyclization/arylation that forges three new C-C bonds.

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