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 Dearomatizing conversion of pyrazines to 1,4-dihydropyrazine derivatives via transition-metal-free diboration, silaboration, and hydroboration.

Literature DB >> 22806333

Dearomatizing conversion of pyrazines to 1,4-dihydropyrazine derivatives via transition-metal-free diboration, silaboration, and hydroboration.

Kazuyuki Oshima¹, Toshimichi Ohmura, Michinori Suginome.

Abstract

Pyrazines and substituted pyrazines undergo addition of boron reagents having B-B, Si-B, and H-B bonds under transition-metal-free conditions, leading to high-yield synthesis of N-borylated 1,4-dihydropyrazines and 1,2,3,4-tetrahydropyrazine.

Entities: Chemical

Year: 2012 PMID： 22806333 DOI： 10.1039/c2cc34086k

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

Keyword Cloud
Cited

7 in total

1. Atom-efficient regioselective 1,2-dearomatization of functionalized pyridines by an earth-abundant organolanthanide catalyst.

Authors: Alexander S Dudnik; Victoria L Weidner; Alessandro Motta; Massimiliano Delferro; Tobin J Marks
Journal: Nat Chem Date: 2014-10-19 Impact factor: 24.427

2. NHC induced radical formation via homolytic cleavage of B-B bonds and its role in organic reactions.

Authors: Laura Kuehn; Ludwig Zapf; Luis Werner; Martin Stang; Sabrina Würtemberger-Pietsch; Ivo Krummenacher; Holger Braunschweig; Emmanuel Lacôte; Todd B Marder; Udo Radius
Journal: Chem Sci Date: 2022-06-07 Impact factor: 9.969

3. Boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with silylborane and an alkoxy base: expanded scope and mechanistic studies.

Authors: Eiji Yamamoto; Satoshi Ukigai; Hajime Ito
Journal: Chem Sci Date: 2015-03-02 Impact factor: 9.825

4. Reactivity of highly Lewis acidic diborane(4) towards pyridine and isocyanide: formation of boraalkene-pyridine complex and ortho-functionalized pyridine derivatives.

Authors: Yuhei Katsuma; Hiroki Asakawa; Makoto Yamashita
Journal: Chem Sci Date: 2017-12-11 Impact factor: 9.825

Dearomatizing conversion of pyrazines to 1,4-dihydropyrazine derivatives via transition-metal-free diboration, silaboration, and hydroboration.

1. Atom-efficient regioselective 1,2-dearomatization of functionalized pyridines by an earth-abundant organolanthanide catalyst.

2. NHC induced radical formation via homolytic cleavage of B-B bonds and its role in organic reactions.

3. Boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with silylborane and an alkoxy base: expanded scope and mechanistic studies.

4. Reactivity of highly Lewis acidic diborane(4) towards pyridine and isocyanide: formation of boraalkene-pyridine complex and ortho-functionalized pyridine derivatives.

5. Super electron donors derived from diboron.

6. Copper-catalyzed silylation of p-quinone methides: new entry to dibenzylic silanes.

7. Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles.