Transition-Metal-Free Tandem Oxidative Removal of Benzylic Methylene Group by C–C and C–N Bond Cleavage Followed by Intramolecular New Aryl C–N Bond Formation under Radical Conditions

2014 ◽  
Vol 16 (17) ◽  
pp. 4392-4395 ◽  
Author(s):  
Joydev K. Laha ◽  
K. S. Satyanarayana Tummalapalli ◽  
Ankur Gupta
Keyword(s):  
Transition Metal ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Metal Free ◽  
Oxidative Removal ◽  
Methylene Group

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...

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...

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

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.

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.

I2/TBHP-Promoted Approach to α-Keto Esters from Trifluoromethyl β-Diketones and Alcohols via C–C Bond Cleavage

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 2018-2023 ◽  
Author(s):  
Xiang Fang ◽  
Xueyan Yang ◽  
Tongle Shao ◽  
Jun Zhou ◽  
Chen Jin ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Mechanistic Studies ◽  
Metal Free ◽  
Oxidation Pathway ◽  
Keto Esters ◽  
Oxidative Coupling Reaction

A metal-free oxidative coupling reaction of trifluoromethyl β-diketones with alcohols for the synthesis of α-keto esters in good to excellent yields has been developed. Preliminary mechanistic studies suggest that an I2/TBHP promoted sequential iodination, C–C bond cleavage, C–O bond formation and oxidation pathway is involved in this reaction.

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