Ligand-Free and Solvent-Free Synthesis of 1,3-Disubstituted Naphthalenes through Stille Coupling

Synlett ◽  
2020 ◽  
Vol 31 (09) ◽  
pp. 903-906
Author(s):  
Taoufik Rohand ◽  
Sanae Sbi ◽  
Victor Mkpenie ◽  
Kiyoshi Tanemura
Keyword(s):  
Functional Groups ◽  
Acetyl Chloride ◽  
Stille Coupling ◽  
Mechanistic Studies ◽  
Major Step ◽  
Mild Conditions ◽  
Synthetic Strategy ◽  
Ligand Free ◽  
Palladium Catalyzed ◽  
Solvent Free Synthesis

A variety of 1,3-disubstituted naphthalenes have been prepared by palladium-catalyzed annulation of (o-ethynylphenyl)acetyl chloride with design of a new synthetic strategy by Stille coupling using functionalized organostannanes. The method affords excellent yields of the substituted naphthalenes and accommodates a wide variety of functional groups under mild conditions. Mechanistic studies show intramolecular cyclization as a major step following C–C bond coupling.

Palladium catalyzed C3-arylation of 4-hydroxy-2-pyridones

2014 ◽  
Vol 50 (52) ◽  
pp. 6879-6882 ◽  
Author(s):  
Elissavet E. Anagnostaki ◽  
Anna D. Fotiadou ◽  
Vera Demertzidou ◽  
Alexandros L. Zografos
Keyword(s):  
Mild Conditions ◽  
Ligand Free ◽  
Palladium Catalyzed ◽  
First Time

The direct 3-arylation of 4-hydroxy-2-pyridones has been achieved for the first time by utilizing ligand free palladium(ii) catalysis under mild conditions.

Palladium-Catalyzed Highly Regioselective ortho-Halogenation of 2-Pyridyl Sulfoxides

Synlett ◽  
2017 ◽  
Vol 28 (10) ◽  
pp. 1232-1236 ◽  
Author(s):  
Meng Sun ◽  
Jun-Long Zhao ◽  
Xiang-Xiang Chen ◽  
Hu Xie ◽  
Jiang-Tao Ren ◽  
...  
Keyword(s):  
Functional Groups ◽  
Activation Pathway ◽  
Mild Conditions ◽  
Palladium Catalyzed

A palladium-catalyzed regioselective ortho-halogenation of 2-pyridyl sulfoxides via a C–H activation pathway has been reported. Under the conditions established, this reaction proceeded smoothly and could tolerate a variety of functional groups under mild conditions.

Access to Chiral γ-Butenolides via Palladium-Catalyzed Asymmetric Allylic C-H Alkylation of 1,4-Dienes

2021 ◽  
Author(s):  
Zhen-Yao Dai ◽  
Pu-Sheng Wang ◽  
Liu-zhu Gong
Keyword(s):  
Functional Groups ◽  
Palladium Catalysis ◽  
Mild Conditions ◽  
Palladium Catalyzed

Asymmetric allylic C-H alkylation of 1,4-pentadienes with α-angelica lactones has been developed by tri-axial phosphoramidite-palladium catalysis. This reaction can tolerate a range of functional groups under mild conditions, furnishing versatile...

Pursuit of Enantioselective Synthesis of Heterocycle-Bearing ­Stereocenters: The Development of a Stereocontrolled BINOL-­Catalyzed Conjugate Addition of Organoboron Nucleophiles

Synlett ◽  
2017 ◽  
Vol 28 (16) ◽  
pp. 2093-2109 ◽  
Author(s):  
Jeremy May ◽  
Thien Nguyen ◽  
Truong Nguyen ◽  
Phong Le ◽  
Po-An Chen ◽  
...  
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Functional Groups ◽  
Conjugate Addition ◽  
Enantioselective Synthesis ◽  
Mechanistic Studies ◽  
Synthetic Strategy ◽  
Iterative Development

This account chronicles the iterative development of an enantioselective conjugate addition of organoboron nucleophiles to α,β-unsaturated enones and enals catalyzed by BINOL derivatives. Beginning with a specific application of this transformation to the total synthesis of the flinderole alkaloids, the transformation progressed to encompass a much larger scope of heterocycle-substituted electrophiles. The next phase saw progress toward the use of a broader scope of functional nucleophiles, with application in a strategy to synthesize discoipyrrole D. At each stage of this chronologically organized discussion, key problems, hypotheses, and solutions are presented to show the sources of discovery and solutions to problems as the catalyst and other reaction components were made more reactive. The interplay of target-directed reaction development, efforts to increase the scope of compatible functional groups, mechanistic studies, and empirical exploration is described to illustrate sources of chemical discovery.1 Introduction2 Synthesis of the Flinderole Natural Products3 Indole-Bearing Stereocenters4 Heteroaryl-Bearing Stereocenters5 Bis-Heteroaryl Stereocenters6 Synthetic Strategy for Discoipyrrole D7 Bis-Aryl Stereocenters8 Remaining Challenges9 Conclusion

Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage–Independent Activation of Strong C–O Bonds

2018 ◽  
Author(s):  
Erin Stache ◽  
Alyssa B. Ertel ◽  
Tomislav Rovis ◽  
Abigail G. Doyle
Keyword(s):  
Carboxylic Acids ◽  
Functional Groups ◽  
Single Step ◽  
Direct Access ◽  
Photoredox Catalysis ◽  
Acyl Radical ◽  
Synthetic Strategy ◽  
Acyl Radicals ◽  
Benzyl Radicals ◽  
Aliphatic Carboxylic Acids

Alcohols and carboxylic acids are ubiquitous functional groups found in organic molecules that could serve as radical precursors, but C–O bonds remain difficult to activate. We report a synthetic strategy for direct access to both alkyl and acyl radicals from these ubiquitous functional groups via photoredox catalysis. This method exploits the unique reactivity of phosphoranyl radicals, generated from a polar/SET crossover between a phosphine radical cation and an oxygen centered nucleophile. We first show the desired reactivity in the reduction of benzylic alcohols to the corresponding benzyl radicals with terminal H-atom trapping to afford the deoxygenated product. Using the same method, we demonstrate access to synthetically versatile acyl radicals which enables the reduction of aromatic and aliphatic carboxylic acids to the corresponding aldehydes with exceptional chemoselectivity. This protocol also transforms carboxylic acids to heterocycles and cyclic ketones via intramolecular acyl radical cyclizations to forge new C–O, C–N and C–C bonds in a single step.

Borates as a Traceless Activation Group for Intermolecular Alkylarylation of Ethylene through Photoredox/Nickel Dual Catalysis

Synlett ◽  
2020 ◽  
Author(s):  
Shengqing Zhu ◽  
Lingling Chu ◽  
Xiaoliang Feng ◽  
Lei Guo
Keyword(s):  
Functional Groups ◽  
Aryl Halides ◽  
Nickel Catalysis ◽  
Mild Conditions ◽  
Dual Catalysis

AbstractA formal ethylene alkylarylation reaction with aryl halides and alkyl oxalates enabled by synergistic photoredox/nickel catalysis is reported. This protocol takes advantage of borates as a traceless activation group, achieving the formal ethylene difunctionalized products via a catalytic three-component 1,2-alkylarylation of vinyl borate followed by a base-assisted deborylation process. The mild conditions allow for excellent functional groups compatibility and broad substrate scope.

Sign in / Sign up

Export Citation Format

Share Document