Cu(I)/Pd(II)-Catalyzed Intramolecular Hydroamidation and C-H Dehydrogenative Coupling of ortho-Alkynyl- N-arylbenzamides for Access to Isoindolo[2,1- a]Indol-6-Ones

Baoxin Tang; Ruimao Hua

doi:10.3390/molecules27113393

Cu(I)/Pd(II)-Catalyzed Intramolecular Hydroamidation and C-H Dehydrogenative Coupling of ortho-Alkynyl- N-arylbenzamides for Access to Isoindolo[2,1- a]Indol-6-Ones

Molecules. 2022 May 25;27(11):3393. doi: 10.3390/molecules27113393.

Authors

Baoxin Tang¹, Ruimao Hua^{1

2}

Affiliations

¹ Department of Chemistry, Tsinghua University, Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Beijing 100084, China.
² College of Chemistry, Xinjiang University, Urumqi 830017, China.

Abstract

An efficient, atom-economic and one-pot synthesis of isoindolo[2,1-a]indol-6-ones via CuI/Pd(OAc)₂-catalyzed intramolecular hydroamidation of alkynyl group, and C-H dehydrogenative coupling of ortho-alkynyl-N-arylbenzamides has been developed. This transformation occurs with the use of oxygen as the oxidant, and water is the only by-product. The reaction shows a high tolerance to a variety of functional groups, and affords isoindolo[2,1-a]indol-6-ones in good to high yields.

Keywords: C-H dehydrogenative coupling; hydroamidation of alkyne; isoindolo[2,1-a]indol-6-one; ortho-alkynyl-N-arylbenzamide.

Grants and funding

21673124, 21972072/National Natural Science Foundation of China