Transition Metal-Free Synthesis of Pinacol Arylboronate: Regioselective Boronation of 1,3-Disubstituted Benzenes

2014 ◽  
Vol 67 (4) ◽  
pp. 675 ◽  
Author(s):  
Yan Wang ◽  
Le Wang ◽  
Ling-Yan Chen ◽  
Pinaki S. Bhadury ◽  
Zhihua Sun
Keyword(s):  
Transition Metal ◽  
Regioselective Synthesis ◽  
Ortho Position ◽  
Metal Free ◽  
Disubstituted Benzene ◽  
Wide Range

The regioselective synthesis of pinacol arylboronate has been achieved from 1,3-disubstituted benzene through directed ortho-metallation (DoM)–borylation sequence. A wide range of substituents and borylating reagents were investigated. In situ lithiation and subsequent boronation predominantly occurred at the ortho-position to afford the desired products in moderate yields.

Insertion Reaction of 2-Halo-N-allylanilines with K2S Involving Trisulfur Radical Anion: Synthesis of Benzothiazole Derivatives under Transition-Metal-Free Conditions

Synthesis ◽  
2020 ◽  
Author(s):  
Yan-Wei Zhao ◽  
Shun-Yi Wang ◽  
Xin-Yu Liu ◽  
Tian Jiang ◽  
Weidong Rao
Keyword(s):  
Transition Metal ◽  
Radical Anion ◽  
Radical Cyclization ◽  
Transition Metal Catalysis ◽  
Insertion Reaction ◽  
Metal Catalysis ◽  
Metal Free ◽  
Benzothiazole Derivatives

AbstractA synthesis of benzothiazole derivatives through the reaction of 2-halo-N-allylanilines with K2S in DMF is developed. The trisulfur radical anion S3·–, which is generated in situ from K2S in DMF, initiates the reaction without transition-metal catalysis or other additives. In addition, two C–S bonds are formed and heteroaromatization of benzothiazole is triggered by radical cyclization and H-shift.

Transition-Metal-Free Cascade Approach toward 2-Alkoxy/2-Sulfenylpyridines and Dihydrofuro[2,3-b]pyridines by Trapping In Situ Generated 1,4-Oxazepine

2017 ◽  
Vol 82 (18) ◽  
pp. 9515-9524 ◽  
Author(s):  
Guolin Cheng ◽  
Lulu Xue ◽  
Yunxiang Weng ◽  
Xiuling Cui
Keyword(s):  
Transition Metal ◽  
Metal Free

A Metal-free and β-Stereoselective Synthesis of 2-Deoxy-C-aryl Glycosides: Synthesis of 5-aza analogues of Aquayamycin

Synlett ◽  
2021 ◽  
Author(s):  
Yuling Mei ◽  
nan jiang ◽  
Yu Yang ◽  
Wan Zhang ◽  
Saifeng Qiu ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Metal Free ◽  
Wide Range ◽  
One Step ◽  
Aryl Glycosides ◽  
Aryl Glycoside

A convenient protocol for β-stereoselective synthesis of 2-deoxy-C-aryl glycosides has been developed. This reaction takes place in one step by using I2/Et3SiH to activate glycosyl acetate to generate glycosyl iodide intermediate in situ, which was captured by naphthol followed by Fries-like O- → C-glycoside rearrangement to selectively afford β-C-aryl glycoside. The approach is applicable to a wide range of naphthol modules, and its utility was demonstrated in the synthesis of 5-aza analogues of Aquayamycin.

ChemInform Abstract: Regioselective Synthesis of Phenoxathiin Derivatives under Transition-Metal-Free Conditions.

ChemInform ◽  
2013 ◽  
Vol 44 (30) ◽  
pp. no-no
Author(s):  
Fangdong Hu ◽  
Xin Zhao ◽  
Yanqiu Li ◽  
Lei Feng ◽  
Chen Ma
Keyword(s):  
Transition Metal ◽  
Regioselective Synthesis ◽  
Metal Free

Deuterated Aryl Alkyl Ethers Synthesis via Nucleophilic Etherification of Aryl Alkyl Ethers and Thioethers with Deuterated Alcohols

Synlett ◽  
2019 ◽  
Vol 30 (15) ◽  
pp. 1805-1809
Author(s):  
Shuai Li ◽  
Xia Wang ◽  
Xin-Ge Yang ◽  
Gui-Quan Yu ◽  
Xue-Qiang Wang
Keyword(s):  
Transition Metal ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Metal Free ◽  
Wide Range ◽  
Alkyl Ethers

A transition-metal-free etherification protocol that is capable of synthesizing deuterated ethers is described. A wide range of aryl alkyl ethers and thioethers were suitable for this transformation owing to the mild reaction conditions. Besides, a series of sterically bulky deuterated alcohols were successfully incorporated into cyano-substituted arenes. The results of mechanistic studies suggested this reaction might take place via nucleophilic aromatic substitution pathway.

Recent Developments in Transition-Metal-Free Functionalization and Derivatization Reactions of Pyridines

Synlett ◽  
2020 ◽  
Author(s):  
Lei Jiao ◽  
Fei-Yu Zhou
Keyword(s):  
Transition Metal ◽  
Structural Motif ◽  
Metal Exchange ◽  
Coupling Reactions ◽  
Phosphonium Salts ◽  
Metal Free ◽  
Radical Coupling ◽  
In Situ Activation ◽  
Recent Developments

AbstractPyridine is an important structural motif that is prevalent in natural products, drugs, and materials. Methods that functionalize and derivatize pyridines have gained significant attention. Recently, a large number of transition-metal-free reactions have been developed. In this review, we provide a brief summary of recent advances in transition-metal-free functionalization and derivatization reactions of pyridines, categorized according to their reaction modes.1 Introduction2 Metalated Pyridines as Nucleophiles2.1 Deprotonation2.2 Halogen–Metal exchange3 Activated Pyridines as Electrophiles3.1 Asymmetric 2-Allylation by Chiral Phosphite Catalysis3.2 Activation of Pyridines by a Bifunctional Activating Group3.3 Alkylation of Pyridines by 1,2-Migration3.4 Alkylation of Pyridines by [3+2] Addition3.5 Pyridine Derivatization by Catalytic In Situ Activation Strategies3.6 Reactions via Heterocyclic Phosphonium Salts4 Radical Reactions for Pyridine Functionalization4.1 Pyridine Functionalization through Radical Addition Reactions4.2 Pyridine Functionalization through Radical–Radical Coupling Reactions5 Derivatization of Pyridines through the Formation of Meisenheimer-Type Pyridyl Anions6 Conclusion

A transition metal-free approach towards the regioselective synthesis of β-carboline tethered pyrroles and 2,3-dihydro-1H-pyrroles

2020 ◽  
Vol 44 (28) ◽  
pp. 12370-12383
Author(s):  
Manpreet Singh ◽  
Avijit Kumar Paul ◽  
Virender Singh
Keyword(s):  
Transition Metal ◽  
Regioselective Synthesis ◽  
One Pot ◽  
Sequential Approach ◽  
Metal Free

A transition metal-free one-pot sequential approach has been unfolded for the synthesis of β-carboline tethered pyrroles and 2,3-dihydro-1H-pyrroles by using highly diverse 1-formyl-9H-β-carbolines as a template.

Chemoselective addition of in situ prepared lithium alkynyl borates to aldehydes: a practical and transition metal free approach toward the synthesis of propargylic alcohols

2010 ◽  
Vol 51 (10) ◽  
pp. 1386-1389 ◽  
Author(s):  
Irene Notar Francesco ◽  
Antoine Renier ◽  
Alain Wagner ◽  
Françoise Colobert
Keyword(s):  
Transition Metal ◽  
Propargylic Alcohols ◽  
Metal Free
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