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

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.

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

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

ChemInform Abstract: In situ Generation of PhI+CF3and Transition-Metal-Free Oxidative sp2C-H Trifluoromethylation.

ChemInform ◽  
2013 ◽  
Vol 44 (48) ◽  
pp. no-no
Author(s):  
Cong Xu ◽  
Jingxin Liu ◽  
Wenbo Ming ◽  
Yingjie Liu ◽  
Jun Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Metal Free ◽  
In Situ Generation

nBu4NOTf-promoted radical self-hydrogen transferring isomerization under transition metal-free conditions

2018 ◽  
Vol 5 (7) ◽  
pp. 1213-1216 ◽  
Author(s):  
Hong-Xing Zheng ◽  
Chuan-Zhi Yao ◽  
Jian-Ping Qu ◽  
Yan-Biao Kang
Keyword(s):  
Transition Metal ◽  
Metal Free

We report the first allylic isomerization of alcohols catalyzed by nBu4NOTf generated in situ from tetrabutylammonium triflate and potassium tert-butoxide.

Diastereoselective synthesis of spiro[cyclopropane-1,3′-indolin]-2′-ones through metal-free cyclopropanation using tosylhydrazone salts

RSC Advances ◽  
2014 ◽  
Vol 4 (72) ◽  
pp. 38425-38432 ◽  
Author(s):  
Jeevak Sopanrao Kapure ◽  
Chada Narsimha Reddy ◽  
Praveen Reddy Adiyala ◽  
Ranjita Nayak ◽  
V. Lakshma Nayak ◽  
...  
Keyword(s):  
Transition Metal ◽  
Diazo Compounds ◽  
Diastereoselective Synthesis ◽  
Metal Free

Anticancer spiro[cyclopropane-1,3′-indolin]-2′-ones are accessible through a transition metal-free diastereoselective cyclopropanation using in situ generated diazo-compounds.

In Situ Generation of PhI+ CF3 and Transition-Metal-Free Oxidative sp2 CH Trifluoromethylation

2013 ◽  
Vol 19 (28) ◽  
pp. 9104-9109 ◽  
Author(s):  
Cong Xu ◽  
Jingxin Liu ◽  
Wenbo Ming ◽  
Yingjie Liu ◽  
Jun Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Metal Free ◽  
In Situ Generation

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.

ChemInform Abstract: Transition-Metal-Free Oxychlorination of Alkenyl Oximes: In situ Generated Radicals with tert-Butyl Nitrite.

ChemInform ◽  
2016 ◽  
Vol 47 (50) ◽  
Author(s):  
Xiao-Wei Zhang ◽  
Zu-Feng Xiao ◽  
Mei-Mei Wang ◽  
Yan-Jun Zhuang ◽  
Yan-Biao Kang
Keyword(s):  
Transition Metal ◽  
Metal Free ◽  
Tert Butyl
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