Synthesis of Sulfonyldiazomethanes and Acetyldiazomethanes via an Alumina-Mediated Decarboxylation Strategy

2016 ◽  
Vol 69 (2) ◽  
pp. 239 ◽  
Author(s):  
Yiyong Yan ◽  
Gaoyuan Ma ◽  
Wei Wei ◽  
Jing Zhao
Keyword(s):  
Organic Synthesis ◽  
Diazo Compounds ◽  
Simple Method ◽  
Neutral Alumina ◽  
Excellent Yield

Diazo compounds are widely adopted in organic synthesis due to their carbine characteristics. One of the most interesting diazo compounds is diazolsulfonyl. Here, in the current study, we found that diazolsufonyl compounds could be prepared with moderate to excellent yield through decarboxylation of diazosulfonyl acetates by neutral alumina. We hope that this mild and simple method might inspire wider application of these useful compounds.

A Mild and Simple Method for Making MIDA Boronates

2020 ◽  
Author(s):  
Aidan Kelly ◽  
Peng-Jui (Ruby) Chen ◽  
Jenna Klubnick ◽  
Daniel J. Blair ◽  
Martin D. Burke
Keyword(s):  
Organic Synthesis ◽  
Boronic Acids ◽  
Simple Method ◽  
Direct Preparation ◽  
Synthesis Procedure ◽  
Harsh Conditions

<div> <div> <div> <p>Existing methods for making MIDA boronates require harsh conditions and complex procedures to achieve dehydration. Here we disclose that a pre-dried form of MIDA, MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in labs that do not specialize in organic synthesis. </p> </div> </div> </div>

Utility of Heterocyclic Diazo Compounds in Organic Synthesis

Heterocycles ◽  
1976 ◽  
Vol 4 (6) ◽  
pp. 1115 ◽  
Author(s):  
Miha Tisler ◽  
Branko Stanovnik
Keyword(s):  
Organic Synthesis ◽  
Diazo Compounds

Recent Developments of Diazo Compounds in Organic Synthesis

10.1142/q0261 ◽  
2021 ◽  
Author(s):  
Di Qiu ◽  
Jianbo Wang
Keyword(s):  
Organic Synthesis ◽  
Diazo Compounds ◽  
Recent Developments

Catalyst-free synthesis of oxazol-2(3H)-ones from sulfilimines and diazo compounds through a tandem rearrangement/aziridination/ring-expansion reaction

2021 ◽  
Author(s):  
Lina Song ◽  
Xianhai Tian ◽  
Chunyu Han ◽  
Mehran Amanpur ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Drug Development ◽  
Organic Synthesis ◽  
Significant Role ◽  
Ring Expansion ◽  
Diazo Compounds ◽  
Catalyst Free ◽  
Ring Expansion Reaction

Oxazol-2(3H)-ones play a significant role in the fields of organic synthesis and drug development.

Aziridinyl imines in organic synthesis: Development of tandem reaction strategies and application to total synthesis of natural products

2013 ◽  
Vol 85 (4) ◽  
pp. 741-753 ◽  
Author(s):  
Hee-Yoon Lee ◽  
Seog-Beom Song ◽  
Taek Kang ◽  
Yoon Jung Kim ◽  
Su Jeong Geum
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Organic Synthesis ◽  
Reactive Intermediates ◽  
Diazo Compounds ◽  
Tandem Reaction ◽  
Cycloaddition Reactions ◽  
Free Radical Reactions ◽  
Sulfur Ylide ◽  
Epoxide Formation

Aziridinyl imines are well-known carbene equivalents because they are precursors of diazo compounds from which reactive intermediates can be produced. These carbene equivalents can be utilized as zwitterionic species, diradicals, or 4π system for cycloaddition reactions. Thus, the intermediates derived from aziridinyl imines have been used in the sulfur-ylide-mediated epoxide formation, tandem free-radical reactions, or cyclopropanation reaction via carbene intermediates to form trimethylenemethane (TMM) diyls, which undergo [2 + 3] cycloaddition reactions to form cyclopentanoids. Diazo compounds generated from aziridinyl imines also react with allenes to form TMM diyls. This reaction was utilized in tandem cycloaddition reactions of linear substrates to form polyquinanes. These tandem reaction strategies were successfully applied to the total synthesis of various cyclopentanoid natural products.

A Mild and Simple Method for Making MIDA Boronates

2020 ◽  
Author(s):  
Aidan Kelly ◽  
Peng-Jui (Ruby) Chen ◽  
Jenna Klubnick ◽  
Daniel J. Blair ◽  
Martin D. Burke
Keyword(s):  
Organic Synthesis ◽  
Boronic Acids ◽  
Simple Method ◽  
Direct Preparation ◽  
Synthesis Procedure ◽  
Harsh Conditions

<div> <div> <div> <p>Existing methods for making MIDA boronates require harsh conditions and complex procedures to achieve dehydration. Here we disclose that a pre-dried form of MIDA, MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in labs that do not specialize in organic synthesis. </p> </div> </div> </div>

ChemInform Abstract: HETEROCYCLIC DIAZO COMPOUNDS AS SYNTHONS IN ORGANIC SYNTHESIS. (REVIEW)

1980 ◽  
Vol 11 (38) ◽  
Author(s):  
M. TISHLER ◽  
B. STANOVNIK
Keyword(s):  
Organic Synthesis ◽  
Diazo Compounds
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