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Abstract
The C3 direct arylation of 1H-indazole and 1H-7-azaindazole has been a significant challenge due to the lack of the reactivity at this position. In this paper, we describe a mild and an efficient synthesis of new series of C3-aryled 1H-indazoles and C3-aryled 1H-7-azaindazoles via a C3 direct arylation using water as solvent. On water, PPh3 was effective as a ligand along with a lower charge of the catalyst Pd(OAc)2 (5 mol%) at 100 °C, leading to C3-aryled 1H-indazoles or C3-aryled 1H-7-azaindazoles in moderate to good yields.
Highlights
In recent years, the C–H activation has risen as an increasingly powerful tool for molecular sciences with notable applications in organic synthesis [1,2,3,4,5]
Our group [36,37] and later Popowycz’s [38] group reported independently that the C3 mol%)arylation as catalyst and ligand, was respectively. Under these reaction conditions, the direct of azaindazoles feasible but using again 1,10-phenanthroline (Phen) as a crucial authorsinfailed to achieve directfor arylation on 1-phenyl-1H-indazole, yet theyInconcluded that,and in this ligand the case of 1H series both 4-azaindazoles and 7-azaindazoles
For the first that atime phosphine (PPh contrary ligands to the bidentate (Phen) of 1H-indazole was feasible fortime, the first withoutligand the use of3),bidentate by employing ligand used in the case of organic solvent, is crucial to achieve the arylation reaction
Summary
The C–H activation has risen as an increasingly powerful tool for molecular sciences with notable applications in organic synthesis [1,2,3,4,5]. In 2012, our group [33] in parallel with the Itami group [34] developed, for the first time, conditions to realize the direct arylation of 1H-indazole series The key of this success was the use of bidentate ligand (1,10-phenanthroline) with a high catalyst. Our group [36,37] and later Popowycz’s [38] group reported independently that the C3 mol%)arylation as catalyst and ligand, was respectively Under these reaction conditions, the direct of azaindazoles feasible but using again 1,10-phenanthroline (Phen) as a crucial authorsinfailed to achieve directfor arylation on 1-phenyl-1H-indazole, yet theyInconcluded that,and in this ligand the case of 1H series both 4-azaindazoles and 7-azaindazoles.
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