Direct Transformation from Arylamines to Aryl Naphthalene-1,8-diamino Boronamides: A Metal-Free Sandmeyer-Type Process

Direct Transformation from Arylamines to Aryl Naphthalene-1,8-diamino Boronamides: A Metal-Free Sandmeyer-Type Process

A direct metal-free transformation from arylamines to aryl naphthalene-1,8-diamino boronamides, a type of masked boronic acid, has been developed based on Sandmeyer-type reactions. A nonsymmetrical diboron reagent, B(pin)-B(dan), was utilized as the borylating reagent, and the B(dan) moiety was tran...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2019-01, Vol.24 (3), p.377
Hauptverfasser: Ding, Siyi, Ma, Qiang, Zhu, Min, Ren, Huaping, Tian, Shaopeng, Zhao, Yuzhen, Miao, Zongcheng
Format: Artikel
Sprache:eng
Schlagworte:
Acids
Amines
Aromatic compounds
Boron
boronamides
Carbon
Chromatography
Communication
Functional groups
metal-free borylation
Naphthalene
NMR
Nuclear magnetic resonance
Organic compounds
Reagents
sandmeyer-type reaction
Solvents
Temperature effects
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Zusammenfassung:A direct metal-free transformation from arylamines to aryl naphthalene-1,8-diamino boronamides, a type of masked boronic acid, has been developed based on Sandmeyer-type reactions. A nonsymmetrical diboron reagent, B(pin)-B(dan), was utilized as the borylating reagent, and the B(dan) moiety was transferred to the aim products selectively. This conversion tolerated a series of functional groups, including chloro, bromo, fluoro, ester, hydroxy, cyano and amide.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24030377