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...

Transition‐Metal‐Free Approaches to Arylsulfones using Benzylic Ammonium Salts through C−N Bond Cleavage

2020 ◽  
Vol 9 (2) ◽  
pp. 247-250 ◽  
Author(s):  
Yishuai Liu ◽  
Haibo Zhu ◽  
Liu Yang ◽  
Zongbo Xie ◽  
Guofang Jiang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Bond Cleavage ◽  
Ammonium Salts ◽  
Metal Free

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

scholarly journals Last Decade of Unconventional Methodologies for the Synthesis of Substituted Benzofurans

Molecules ◽  
2020 ◽  
Vol 25 (10) ◽  
pp. 2327 ◽  
Author(s):  
Lucia Chiummiento ◽  
Rosarita D’Orsi ◽  
Maria Funicello ◽  
Paolo Lupattelli
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Intramolecular Cyclization ◽  
Bond Formation ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Metal Free ◽  
Bond Forming ◽  
Intermolecular Cyclization

This review describes the progress of the last decade on the synthesis of substituted benzofurans, which are useful scaffolds for the synthesis of numerous natural products and pharmaceuticals. In particular, new intramolecular and intermolecular C–C and/or C–O bond-forming processes, with transition-metal catalysis or metal-free are summarized. (1) Introduction. (2) Ring generation via intramolecular cyclization. (2.1) C7a–O bond formation: (route a). (2.2) O–C2 bond formation: (route b). (2.3) C2–C3 bond formation: (route c). (2.4) C3–C3a bond formation: (route d). (3) Ring generation via intermolecular cyclization. (3.1) C7a-O and C3–C3a bond formation (route a + d). (3.2) O–C2 and C2–C3 bond formation: (route b + c). (3.3) O–C2 and C3–C3a bond formation: (route b + d). (4) Benzannulation. (5) Conclusion.

Transition-metal-free oxidative carboazidation of acrylamides via cascade C–N and C–C bond-forming reactions

2014 ◽  
Vol 12 (25) ◽  
pp. 4329-4334 ◽  
Author(s):  
Jun Qiu ◽  
Ronghua Zhang
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Efficient Method ◽  
Bond Formation ◽  
Cascade Process ◽  
Metal Free ◽  
Bond Forming ◽  
Bond Forming Reactions ◽  
Radical Cascade ◽  
Novel Strategy

A novel transition-metal-free oxidative carboazidation of acrylamides using inexpensive NaN3 and K2S2O8 was achieved, which not only provided an efficient method to prepare various N3-substituted oxindoles, but also represented a novel strategy for C–N and C–C bond formation via a free-radical cascade process.

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.

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