Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 A direct synthesis of allenes by a traceless Petasis reaction.

Literature DB >> 22452672

A direct synthesis of allenes by a traceless Petasis reaction.

Devon A Mundal¹, Kelly E Lutz, Regan J Thomson.

Abstract

A one-pot synthesis of allenes by the 2-nitrobenzenesulfonylhydrazide-mediated coupling of hydroxyaldehydes or ketones with alkynyl trifluoroborate salts is reported. This mild process involves in situ formation of a sulfonylhydrazone that reacts with alkynyl trifluoroborates to generate a transient propargylic hydrazide species. Decomposition of this unstable hydrazide via an intermediate monoalkyldiazine produces the allene products through an alkene walk mechanism.

Entities: Chemical Disease

Year: 2012 PMID： 22452672 DOI： 10.1021/ja301489n

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

Keyword Cloud
Cited

11 in total

1. Organo-manganese η2-auxiliary directed reactions: a diastereoselective approach to 2,3-allenols.

Authors: Animesh Roy; Bilal A Bhat; Salvatore D Lepore
Journal: Org Lett Date: 2015-02-09 Impact factor: 6.005

2. Asymmetric Protonation of Cumulenolates: Synthesis of Allenyl Aldehydes Facilitated by an Organomanganese Auxiliary.

Authors: Animesh Roy; Bilal A Bhat; Salvatore D Lepore
Journal: Org Lett Date: 2016-02-29 Impact factor: 6.005

3. Functionalized Spiroindolines with Anticancer Activity through a Metal-Free Post-Ugi Diastereoselective One-Pot Cascade Reaction.

Authors: Zhi-Gang Xu; Shi-Qiang Li; Jiang-Ping Meng; Dian-Yong Tang; Liu-Jun He; Jie Lei; Hui-Kuan Lin; Hong-Yu Li; Zhong-Zhu Chen
Journal: Chemistry Date: 2018-04-20 Impact factor: 5.236

A direct synthesis of allenes by a traceless Petasis reaction.

1. Organo-manganese η2-auxiliary directed reactions: a diastereoselective approach to 2,3-allenols.

2. Asymmetric Protonation of Cumulenolates: Synthesis of Allenyl Aldehydes Facilitated by an Organomanganese Auxiliary.

3. Functionalized Spiroindolines with Anticancer Activity through a Metal-Free Post-Ugi Diastereoselective One-Pot Cascade Reaction.

4. Carbon-Nitrogen Bond Formation via the Vanadium Oxo Catalyzed Sigmatropic Functionalization of Allenols.

5. Enantioselective Synthesis of Allenes by Catalytic Traceless Petasis Reactions.

6. Divergent, C-C Bond Forming Macrocyclizations Using Modular Sulfonylhydrazone and Derived Substrates.

7. Asymmetric Traceless Petasis Borono-Mannich Reactions of Enals: Reductive Transposition of Allylic Diazenes.

8. Reactivity and Synthetic Applications of Multicomponent Petasis Reactions.

9. Catalyst-Free One-Pot Synthesis of Densely Substituted Pyrazole-Pyrazines as Anti-Colorectal Cancer Agents.

Review 10. Chiral Diol-Based Organocatalysts in Enantioselective Reactions.