Visible-Light-Driven Halogen-Bond-Assisted Direct Synthesis of Heteroaryl Thioethers Using Transition-Metal-Free One-Pot C–I Bond Formation/C–S Cross-Coupling Reaction

2021 ◽  
Vol 86 (3) ◽  
pp. 2570-2581
Author(s):  
Anuradha Nandy ◽  
Imran Kazi ◽  
Somraj Guha ◽  
Govindasamy Sekar
Keyword(s):  
Transition Metal ◽  
Halogen Bond ◽  
Direct Synthesis ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
One Pot ◽  
Metal Free ◽  
Cross Coupling Reaction ◽  
Visible Light Driven

An Iodide-Mediated Transition-Metal-Free Strategy towards Unsymmetrical Diaryl Sulfides via Arylhydrazines and Thiols

Synthesis ◽  
2019 ◽  
Vol 52 (05) ◽  
pp. 727-734 ◽  
Author(s):  
Farnaz Jafarpour ◽  
Mohammad Asadpour ◽  
Meysam Azizzade ◽  
Mehran Ghasemi ◽  
Saideh Rajai-Daryasarei
Keyword(s):  
Transition Metal ◽  
Room Temperature ◽  
Bond Formation ◽  
Antidepressant Drug ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Potential Utility ◽  
Metal Free ◽  
Cross Coupling Reaction ◽  
High Yields

A mild, scalable iodine-mediated oxidative cross-coupling reaction of arylhydrazines and thiols for construction of thioethers (sulfides) in the absence of any transition metals or photocatalysts is disclosed. A variety of unsymmetrical diaryl sulfides with broad substrate scope both on thiols and hydrazines were synthesized in high yields in water at room temperature. Furthermore, to demonstrate the utility of the protocol, the above C–S bond formation was applied in the synthesis of the key structure of vortioxetine as an antidepressant drug. The gram-scale outcome also added to the potential utility of this protocol.

Unexpected CN bond formation via NaI-catalyzed oxidative de-tetra-hydrogenative cross-couplings between N,N-dimethyl aniline and sulfamides

RSC Advances ◽  
2015 ◽  
Vol 5 (62) ◽  
pp. 50113-50117 ◽  
Author(s):  
Yang Zheng ◽  
Jincheng Mao ◽  
Jie Chen ◽  
Guangwei Rong ◽  
Defu Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Metal Free ◽  
Cross Coupling Reaction

A direct de-tetra-hydrogenative cross-coupling reaction between Csp3–H bonds and sulfamide under transition-metal-free conditions is reported to give the corresponding amidines.

Potassium tert-Butoxide Mediated Reductive C–P Cross-Coupling of Arylvinyl Sulfides through C–S Bond Cleavage

Synlett ◽  
2020 ◽  
Author(s):  
Qingle Zeng ◽  
Jie Feng ◽  
Qiaoling Zhang ◽  
Fuhai Li ◽  
Lu Yang ◽  
...  
Keyword(s):  
Double Bond ◽  
Transition Metal ◽  
Bond Cleavage ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Phosphine Oxides ◽  
One Pot ◽  
Metal Free ◽  
Cross Coupling Reaction

AbstractA transition-metal-free t-BuOK-mediated reductive C–P cross-coupling reaction of arylvinyl sulfides with diarylphosphine oxides through C–S bond cleavage has been developed. This protocol not only permits the synthesis of diaryl(2-arylethyl)phosphine oxides, but also achieves an unprecedented construction of a C–P bond through C–S bond cleavage and reduction of a C–C double bond in one pot.

ChemInform Abstract: A Transition-Metal-Free Cross-Coupling Reaction of Allylic Bromides with Aryl- and Vinylboronic Acids.

ChemInform ◽  
2012 ◽  
Vol 43 (33) ◽  
pp. no-no
Author(s):  
Mitsuhiro Ueda ◽  
Kota Nishimura ◽  
Ryo Kashima ◽  
Ilhyong Ryu
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Metal Free ◽  
Cross Coupling Reaction

Transition metal-free tandem pyridinyl–allyl–allyl cross-coupling reaction

2017 ◽  
Vol 47 (18) ◽  
pp. 1668-1675 ◽  
Author(s):  
Lili Zhang ◽  
Zhengkai Chen ◽  
Hongli Li ◽  
Wenguang Yin ◽  
Jianfeng Xu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Metal Free ◽  
Cross Coupling Reaction

Ni-Catalyzed Deamination Cross-Electrophile Coupling of Katritzky Salts with Halides via C–N Bond Activation

2019 ◽  
Author(s):  
Shengyang Ni ◽  
Chunxiao Li ◽  
Jianlin Han ◽  
Yu Mao ◽  
Yi Pan
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
One Pot ◽  
Aryl Iodide ◽  
Cross Coupling Reaction ◽  
New Strategy ◽  
The Cross

This work describes the first Ni-catalyzed cross-electrophile coupling of alkylpyridinium salts, derived from the corresponding amines, with aryl iodide, bromoalkyne or bromoalkyl coupling partners. C(sp)-C(sp<sup>3</sup>), C(sp<sup>2</sup>)-C(sp<sup>3</sup>) and C(sp<sup>3</sup>)-C(sp<sup>3</sup>) bond formation was achieved to afford a variety of synthetically useful arenes, alkynes and alkanes in good yields from<b>2</b>-<b>33</b>. The advantages of the methodology are showcased in the two-step synthesis of the key lactonic moiety of (+)-Compactin and (+)-Mevinolin from commercially available starting materials. A one-pot procedure without isolation of alkylpyridinium tetrafluoroborate salt was also demonstrated to be successful. This work represents a new strategy for the cross-coupling reaction of two electrophiles, and also provides a complementary and highly valuable vista for the current methodologies of alkyl arene/alkyne/alkane synthesis.

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