Transition-metal-free aerobic C–O bond formation via C–N bond cleavage

2020 ◽  
Vol 7 (9) ◽  
pp. 1077-1081
Author(s):  
Lirong Guo ◽  
Fengting Liu ◽  
Liying Wang ◽  
Hairui Yuan ◽  
Lei Feng ◽  
...  
Keyword(s):  
Transition Metal ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Metal Free ◽  
Mild Conditions ◽  
Efficient Construction

We disclosed a TM-free cascade SNAr-[3,3] rearrangement–rearomatization process for the efficient construction of NOBIN-type biaryls from readily available (hetero)arylhydroxylamines and aryltrimethylammonium salts under mild conditions.

Conversion of Esters to Thioesters under Mild Conditions

2021 ◽  
Author(s):  
Yijun Shi ◽  
Xuejing Liu ◽  
Han Cao ◽  
Fusheng Bie ◽  
Ying Han ◽  
...  
Keyword(s):  
Transition Metal ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Free System ◽  
Metal Free ◽  
Mild Conditions

We report conversion of esters to thioesters via selective C–O bond cleavage/weak C–S bond formation under transition-metal-free conditions. The method is notable for a general and practical transition-metal-free system, broad...

Metal-free n-Et4NBr-catalyzed radical cyclization of disulfides and alkynes leading to benzothiophenes under mild conditions

RSC Advances ◽  
2014 ◽  
Vol 4 (89) ◽  
pp. 48547-48553 ◽  
Author(s):  
Daoshan Yang ◽  
Kelu Yan ◽  
Wei Wei ◽  
Laijin Tian ◽  
Qinghe Li ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Bond Formation ◽  
Environmentally Friendly ◽  
Radical Cyclization ◽  
Title Reaction ◽  
Metal Free ◽  
Mild Conditions

The title reaction involves metal free TEAB-catalyzed S–S bond cleavage, C–S bond formation and C–C bond formation; it uses readily available disulfides and alkynes as substrates, and environmentally friendly TEAB as catalyst to synthesize useful benzothiophene derivatives.

Effective, transition metal free and selective C–F activation under mild conditions

RSC Advances ◽  
2015 ◽  
Vol 5 (10) ◽  
pp. 7035-7048 ◽  
Author(s):  
Xianqiang Kong ◽  
Huizi Zhang ◽  
Yunqing Xiao ◽  
Changsheng Cao ◽  
Yanhui Shi ◽  
...  
Keyword(s):  
Transition Metal ◽  
Aromatic Amines ◽  
Bond Cleavage ◽  
Metal Free ◽  
Mild Conditions

A simple and effective aromatic nucleophilic monosubstitution reaction for the synthesis of aromatic amines via selective C–F bond cleavage of various fluoroarenes with primary and secondary aromatic amines is demonstrated.

Transition-metal-free and base promoted C–C bond formation via C–N bond cleavage of organoammonium salts

2021 ◽  
Author(s):  
Tao Zhang ◽  
Kunyu Wang ◽  
Yuting Ke ◽  
Yuanyuan Tang ◽  
Long Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Ammonium Salts ◽  
Metal Free ◽  
Bond Forming ◽  
Benzyl Ammonium

A transition-metal-free and base promoted C–C bond forming reaction of benzyl C(sp3)-H bond with organoammonium salts via C–N bond cleavage has been reported. Benzyl ammonium salts as well as cinnamyl...

Pyridine-mediated B-B Bond Activation of (RO)2B-B(OR)2 for Generating Borylpyridine Anions and Pyridine-stabilized Boryl Radicals as Useful Boryl Reagents in Organic Synthesis

Synthesis ◽  
2021 ◽  
Author(s):  
Luis Carlos Misal Castro ◽  
Ibrahim Sultan ◽  
Hayato Tsurugi ◽  
Kazushi Mashima
Keyword(s):  
Transition Metal ◽  
Organic Synthesis ◽  
Bond Activation ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Pyridine Derivatives ◽  
Organic Transformations ◽  
Lewis Bases ◽  
Metal Free ◽  
Synthetic Utility

Significant developments have been achieved in recent years toward the utilization of (RO)2B-B(OR)2 for exploring transition metal-free organic transformations in organic synthesis. Among the various combinations of Lewis bases with diborons developed so far, pyridine-derivatives are simple, commercially available, and cheap compounds to expand the synthetic utility of diborons by generating borylpyridine anions and pyridine-stabilized boryl radicals via the B-B bond cleavage. These borylpyridine species mediate a series of transformations in both a catalytic and stoichiometric manner for C-X activation (X = Halogen, CO2H, NR2) and concomitant C-borylation, hydroboration, C-C bond formation, and reduction reactions.

Transition-Metal-Free Aryl–Heteroatom Bond Formation via C–S Bond Cleavage

2019 ◽  
Vol 21 (18) ◽  
pp. 7303-7306 ◽  
Author(s):  
Jian-Nan Zhao ◽  
Muzaffar Kayumov ◽  
Dong-Yu Wang ◽  
Ao Zhang
Keyword(s):  
Transition Metal ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Metal Free

Dearomative C–C and C–N bond cleavage of 2-arylindoles: transition-metal-free access to 2-aminoarylphenones

2016 ◽  
Vol 3 (3) ◽  
pp. 364-367 ◽  
Author(s):  
Shuang Luo ◽  
Ziwei Hu ◽  
Qiang Zhu
Keyword(s):  
Transition Metal ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Environmentally Benign ◽  
Free Access ◽  
Oxidative Dearomatization ◽  
Metal Free

A transition-metal-free conversion of 2-arylindoles to 2-aminoarylphenones, using environmentally benign O2 as the sole oxidant, has been developed. This novel oxidative dearomatization process involves cleavage of two C–C and one C–N bonds followed by new C–C and C–O bond formation.

A Sequential Ugi-Smiles / Transition-Metal-Free Endo-Dig Conia-ene Cyclization: The Selective Synthesis of Saccharin Substituted 2,5-dihydropyrroles

2021 ◽  
Author(s):  
Hassan Seyrani ◽  
Sorour Ramezanpour ◽  
Aref Vaezghaemi ◽  
Farzad Kobarfard
Keyword(s):  
Transition Metal ◽  
Free Access ◽  
Selective Synthesis ◽  
Metal Free ◽  
Mild Conditions

A convenient, transition-metal-free access to a series of unprecedented saccharin substituted 2,5-dihydropyrroles is reported. This approach employs a post-Ugi-Smiles 5-endo-dig Conia-ene cyclization sequence in mild conditions while incorporating a series...

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