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Nickel-catalyzed C-H/N-H annulation of aromatic amides with alkynes in the absence of a specific chelation system.

ABSTRACT: The Ni-catalyzed reaction of aromatic amides with alkynes in the presence of KOBu ^t involves C-H/N-H oxidative annulation to give 1(2H)-isoquinolinones. A key to the success of the reaction is the use of a catalytic amount of strong base, such as KOBu ^t . The reaction shows a high functional group compatibility. The reaction with unsymmetrical alkynes, such as 1-arylalkynes, gives the corresponding 1(2H)-isoquinolinones with a high level of regioselectivity. This discovery would lead to the development of Ni-catalyzed chelation-assisted C-H functionalization reactions without the need for a specific chelation system.

SUBMITTER: Obata A

PROVIDER: S-EPMC5625264 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

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Nickel-catalyzed C-H/N-H annulation of aromatic amides with alkynes in the absence of a specific chelation system.

Obata Atsushi A Ano Yusuke Y Chatani Naoto N

Chemical science 20170724 9

The Ni-catalyzed reaction of aromatic amides with alkynes in the presence of KOBu t involves C-H/N-H oxidative annulation to give 1(2H)-isoquinolinones. A key to the success of the reaction is the use of a catalytic amount of strong base, such as KOBu t . The reaction shows a high functional group compatibility. The reaction with unsymmetrical alkynes, such as 1-arylalkynes, gives the corresponding 1(2H)-isoquinolinones with a high level of regio ...[more]

PMID: 28989692

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