Synthesis 2023; 55(21): 3515-3525
DOI: 10.1055/a-2048-8030
special topic
C–H Bond Functionalization of Heterocycles

Palladium-Catalyzed Regioselective C-Arylation and C,N-Diarylation of N-Aryl-2,3-dihydrophthalazine-1,4-diones Using Diaryliodonium Salts

Sushma Naharwal
a   Department of Chemistry, Birla Institute of Technology and Science, Pilani, Rajasthan 333031, India
,
Narendra Dinkar Kharat
a   Department of Chemistry, Birla Institute of Technology and Science, Pilani, Rajasthan 333031, India
,
Chikkagundagal K. Mahesha
a   Department of Chemistry, Birla Institute of Technology and Science, Pilani, Rajasthan 333031, India
,
Kiran Bajaj
b   Department of Chemistry, Amity Institute of Applied Sciences, Amity University, Noida, Uttar Pradesh, India
,
Rajeev Sakhuja
a   Department of Chemistry, Birla Institute of Technology and Science, Pilani, Rajasthan 333031, India
b   Department of Chemistry, Amity Institute of Applied Sciences, Amity University, Noida, Uttar Pradesh, India
› Author Affiliations
S.N. is thankful to the Council of Scientific and Industrial Research (CSIR), New Delhi for providing a Junior Research Fellowship. N.K.D. and C.K.M. are thankful to the Birla Institute of Technology and Science, Pilani, for providing Junior and Senior Research Fellowships, respectively. The authors acknowledge the Science and Engineering Research Board (SERB), New Delhi, for providing a research grant (CRG/2021/000131).


Abstract

Regioselective C-arylation and C,N-diarylation in 2-aryl-2,3-dihydrophthalazine-1,4-diones has been successfully accomplished with diaryliodonium salts under base-mediated slightly modified Pd-catalyzed conditions. These ligand-driven transformations provided a variety of diversely decorated bi(hetero)aryls in good-to-excellent yields, while N-arylated product could be obtained under similar Pd-catalyzed conditions in the absence of a ligand.

Supporting Information



Publication History

Received: 29 January 2023

Accepted after revision: 07 March 2023

Accepted Manuscript online:
07 March 2023

Article published online:
13 April 2023

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