Synthesis of Ortho-Arylated and Alkenylated Benzamides by Palladium-Catalyzed Denitrogenative Cross-Coupling Reactions of 1,2,3-Benzotriazin-4(3H)‑Ones with Organoboronic Acids

Organoboronic Acids ◽

An efficient palladium-catalyzed denitrogenative Suzuki-Miyaura type cross-coupling of 1,2,3-benzotriazin-4(3H) ones with organoboronic acid is described. The reaction is compatible with various aryl and alkenyl boronic acids affording ortho-arylated and alkenylated...

Palladium catalyzed ligand-free Suzuki cross-coupling reactions of benzylic halides with aryl boronic acids under mild conditions

Tetrahedron Letters ◽

10.1016/j.tetlet.2004.07.073 ◽

2004 ◽

Vol 45 (37) ◽

pp. 6959-6962 ◽

Cited By ~ 67

Author(s):

B.P. Bandgar ◽

Sampada V. Bettigeri ◽

Jaywant Phopase

Keyword(s):

Cross Coupling ◽

Boronic Acids ◽

Coupling Reactions ◽

Mild Conditions ◽

Ligand Free ◽

Nickel‐ and Palladium‐Catalyzed Cross‐Coupling Reactions of Organostibines with Organoboronic Acids

Angewandte Chemie ◽

10.1002/ange.202011491 ◽

2020 ◽

Author(s):

Dejiang Zhang ◽

Liyuan Le ◽

Renhua Qiu ◽

Wai‐Yeung Wong ◽

Nobuaki Kambe

Keyword(s):

Cross Coupling ◽

Coupling Reactions ◽

Organoboronic Acids ◽

Synthesis of Novel Annulated Hymenialdisine Analogues via Palladium-Catalyzed Cross-Coupling Reactions with Aryl Boronic Acids

Synlett ◽

10.1055/s-0029-1218573 ◽

2009 ◽

Vol 2010 (02) ◽

pp. 211-214

Author(s):

Man-Kin Tse ◽

Naveenkumar Mangu ◽

Anke Spannenberg ◽

Matthias Beller

Keyword(s):

Cross Coupling ◽

Boronic Acids ◽

Coupling Reactions ◽

Palladium-Catalyzed Ligand-Free Suzuki Cross-Coupling Reactions of Benzylic Halides with Aryl Boronic Acids under Mild Conditions.

ChemInform ◽

10.1002/chin.200450058 ◽

2004 ◽

Vol 35 (50) ◽

Author(s):

B. P. Bandgar ◽

Sampada V. Bettigeri ◽

Jaywant Phopase

Keyword(s):

Cross Coupling ◽

Boronic Acids ◽

Coupling Reactions ◽

Mild Conditions ◽

Ligand Free ◽

Palladium-Catalyzed Suzuki Cross-Coupling of 2-Halo-Deazapurines with Potassium Organotrifluoroborate Salts in the Regioselective Synthesis of Imidazo[4,5-b]pyridine Analogues

Australian Journal of Chemistry ◽

10.1071/ch15420 ◽

2016 ◽

Vol 69 (6) ◽

pp. 618 ◽

Cited By ~ 10

Author(s):

Bhaskaran Savitha ◽

Ayyiliath. M. Sajith ◽

M. Nibin Joy ◽

K.K. Abdul Khader ◽

A. Muralidharan ◽

...

Keyword(s):

Comparative Study ◽

Cross Coupling ◽

Reaction Rates ◽

Boronic Acids ◽

Coupling Reactions ◽

Coupling Process ◽

Substantial Role ◽

Palladium Catalyzed ◽

High Yields

In this paper, we report the use of potassium organotrifluoroborate salts as nucleophilic organoboron reagents in the Suzuki cross-coupling reactions of 2-halo deazapurines. Regio-isomeric C-2-substituted imidazo[4,5-b]pyridine analogues were synthesized by employing this protocol in good to excellent yields. Whereas aryl and heteroaryl trifluoroborates reacted readily to give the coupled products in high yields, alkyltrifluoroborates were found to be less reactive. The utilization of tetrabutylammonium acetate was found to play a substantial role in enhancing the reaction rates of the cross-coupling process. Also, a comparative study was performed between boronic acids and potassium organotrifluoroborate salts.