Ni-Catalyzed Reductive Difunctionalization of Alkenes

Synthesis ◽  
2020 ◽  
Vol 52 (07) ◽  
pp. 979-992 ◽  
Author(s):  
Yuanyuan Ping ◽  
Wangqing Kong
Keyword(s):  
Double Bond ◽  
Reductive Cyclization ◽  
Recent Advances ◽  
Aryl Amination ◽  
Internal Alkynes ◽  
Alkene Difunctionalization

Alkene difunctionalization represents one of the most efficient methods to synthesize highly functionalized molecules from simple and readily available starting materials. In contrast to the well-established redox-neutral alkene difunctionalization reactions, reductive alkene difunctionalization, which simultaneously introduces two electrophiles on both sides of the double bond, has been much less developed, especially in enantioselective manner. This review summarizes recent advances in the nickel-catalyzed reductive difunctionalization of alkenes and highlights the enantioselective transformations.1 Introduction2 Nickel-Catalyzed Racemic Reductive Difunctionalization of Alkenes3 Nickel-Catalyzed Enantioselective Reductive Difunctionalization of Alkenes3.1 Diarylation of Alkenes3.2 Aryl-alkenylation of Alkenes3.3 Aryl-monofluoroalkenylation of Alkenes3.4 Reductive Cyclization/Coupling with Alkynyl Bromides or Asymmetric Internal Alkynes3.5 Aryl-alkylation of Alkenes3.6 Aryl-amination of Alkenes4 Summary and Outlook

Recent Advances in Piperazine Synthesis

Synthesis ◽  
2017 ◽  
Vol 49 (12) ◽  
pp. 2589-2604 ◽  
Author(s):  
Kristen Gettys ◽  
Zhishi Ye ◽  
Mingji Dai
Keyword(s):  
Transition Metal ◽  
Small Molecule ◽  
Ring System ◽  
Reductive Cyclization ◽  
The Third ◽  
Methods Development ◽  
Recent Advances ◽  
Borrowing Hydrogen ◽  
Palladium Catalyzed ◽  
Metal Catalyzed

Piperazine ranks as the third most common N-heterocycle appearing in small-molecule pharmaceuticals. This review highlights recent advances in methods development for the construction of the piperazine­ ring system with particular emphasis on preparing carbon-substituted piperazines.1 Introduction2 Reduction of (Di)ketopiperazine3 N-Alkylation4 Transition-Metal-Catalyzed/Mediated Piperazine Synthesis4.1 The SnAP and SLAP Methods4.2 Palladium-Catalyzed Cyclization4.3 Gold-Catalyzed Cyclization4.4 Other Metal-Catalyzed/Mediated Cyclization4.5 Borrowing Hydrogen Strategy4.6 Imine Reductive Cyclization5 Reduction of Pyrazines6 Miscellaneous7 Conclusion

Pd-Catalyzed Domino Reactions Involving Alkenes To Access Substituted Indole Derivatives

Synthesis ◽  
2020 ◽  
Vol 52 (19) ◽  
pp. 2731-2760
Author(s):  
Egle M. Beccalli ◽  
Michael S. Christodoulou ◽  
Francesca Foschi ◽  
Sabrina Giofrè
Keyword(s):  
Double Bond ◽  
The Other ◽  
Indole Derivatives ◽  
Domino Reactions ◽  
Recent Advances ◽  
Other Hand ◽  
Palladium Catalyzed ◽  
Intermolecular Reactions

Palladium-catalyzed domino reactions are advanced tools in achieving various nitrogen-containing heterocycles in an efficient and economical manner due to the reduced number of steps in the process. This review highlights recent advances in domino processes aimed at the synthesis of indole derivatives and polycyclic systems containing the indole nucleus in intra/intra- or intra/intermolecular reactions. In particular, we consider domino processes that involve a double bond in a step of the sequence, which allow the issue of regioselectivity in the cyclization to be faced and overcome. The different sections in this review focus on the synthesis of the indole nucleus and functionalization of the scaffold starting from different substrates that have been identified as activated starting materials, which involve a halogenated moiety or unactivated unsaturated systems. In the former case, the reaction is under Pd(0) catalysis, and in the second case a Pd(II) catalytic species is required and then an oxidant is necessary to reconvert the Pd(0) into the active Pd(II) species. On the other hand, the second method has the advantage that it uses easy available and inexpensive substrates.1 Introduction2 Indole Scaffold Synthesis2.1 Activated Substrates2.2 Unactivated Substrates3 Functionalization of Indole Scaffold3.1 Activated Substrates3.2 Unactivated Substrates4 Conclusions

scholarly journals Oxidative and reductive cyclization in stiff dithienylethenes

2018 ◽  
Vol 14 ◽  
pp. 2812-2821 ◽  
Author(s):  
Michael Kleinwächter ◽  
Ellen Teichmann ◽  
Lutz Grubert ◽  
Martin Herder ◽  
Stefan Hecht
Keyword(s):  
Double Bond ◽  
Redox Potential ◽  
Electrochemical Behavior ◽  
Ring Closure ◽  
Reductive Cyclization ◽  
Ring Size ◽  
Major Pathway ◽  
Double Bond Isomerization ◽  
Almost All

The electrochemical behavior of stiff dithienylethenes, undergoing double bond isomerization in addition to ring-closure, has been investigated. Electrochromism was observed in almost all cases, with the major pathway being the oxidatively induced cyclization of the open isomers. The influence of the ring size (to lock the reactive antiparallel conformation) as well as substituents (to modulate the redox potential) on the electrocyclization was examined. In the series of derivatives with 6-membered rings, both the E- and the Z-isomer convert to the closed isomer, whereas for the 7-membered rings no cyclization from the E-isomer was observed. For both stiff and normal dithienylethenes bearing benzonitrile substituents an additional and rare reductive electrocyclization was observed. The mechanism underlying both observed electrocyclization pathways has been elucidated.

scholarly journals Recent Advances in Aryne Double Bond Insertion

2015 ◽  
Vol 35 (4) ◽  
pp. 770 ◽  
Author(s):  
Chunrui Wu ◽  
Yupo Yang ◽  
Feng Shi
Keyword(s):  
Double Bond ◽  
Recent Advances

scholarly journals Recent Advances in Functionalization of Double Bond Based on Maleimides

2019 ◽  
Vol 39 (9) ◽  
pp. 2412
Author(s):  
Zhenhua Yang ◽  
Jianan Zhu ◽  
Caiyue Wen ◽  
Yingxiang Ge ◽  
Shengyin Zhao
Keyword(s):  
Double Bond ◽  
Recent Advances

Recent advances in nucleophile-triggered CO2-incorporated cyclization leading to heterocycles

2019 ◽  
Vol 48 (1) ◽  
pp. 382-404 ◽  
Author(s):  
Sheng Wang ◽  
Chanjuan Xi
Keyword(s):  
Reductive Cyclization ◽  
Recent Advances

CO2, as a sustainable, feasible, abundant one-carbon synthon, has been utilized in carboxylative cyclization, carbonylative cyclization, and reductive cyclization.

Coupling of Internal Alkynes in TpMe2Ir Derivatives:  Selective Oxidation of a Noncoordinated Double Bond of the Resulting Iridacycloheptatrienes

2003 ◽  
Vol 125 (6) ◽  
pp. 1478-1479 ◽  
Author(s):  
Eleuterio Álvarez ◽  
Margarita Gómez ◽  
Margarita Paneque ◽  
Cristina M. Posadas ◽  
Manuel L. Poveda ◽  
...  
Keyword(s):  
Double Bond ◽  
Selective Oxidation ◽  
Internal Alkynes

Efficient stereoselective syntheses of piperidine, pyrrolidine, and indolizidine alkaloids

2001 ◽  
Vol 73 (3) ◽  
pp. 573-578 ◽  
Author(s):  
Dieter Enders ◽  
Christoph Thiebes
Keyword(s):  
Double Bond ◽  
Enantioselective Synthesis ◽  
Mexican Bean Beetle ◽  
Indolizidine Alkaloids ◽  
Recent Advances ◽  
Bean Beetle ◽  
Pyrrolidine Alkaloids ◽  
Stereoselective Syntheses ◽  
Enantioselective Syntheses

Recent advances in the diastereo- and enantioselective synthesis of piperidine, pyrrolidine, and indolizidine alkaloids, based on the highly stereoselective 1,2-addition to the CN double bond of chiral aldehyde-SAMP/RAMP hydrazones, are described. The enantioselective syntheses of the pyrrolidine alkaloids bgugaine and (2S,12¢R)-2-(12¢-aminotridecyl)-pyrrolidine, a defense alkaloid of the Mexican bean beetle are reported. Furthermore, the SAMP/RAMP-hydrazone method was applied to the syntheses of two 5,8-disubstituted indolizidine alkaloids that have been extracted from neotropical poison-dart frogs. The a-alkylation of aldehyde-SAMP/RAMP hydrazones has been used in the enantioselective synthesis of two epimers of stenusine, a 3-substituted piperidine alkaloid and spreading reagent of the beetle Stenus comma.

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