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Efficient synthesis of primary and secondary amides via reacting esters with alkali metal amidoboranes.

ABSTRACT: Amides are one of the most important organic compounds that are widely applied in medicine, biochemistry, and materials science. To find an efficient synthetic method of amides is a challenge for organic chemistry. We report here a facile synthesis method of primary and secondary amides through a direct amidation of esters with sodium amidoboranes (NaNHRBH₃, R = H, Me), at room temperature without using catalysts and other reagents. This process is rapid and chemoselective, and features quantitative conversion and wide applicability for esters tolerating different functional groups. The experimental and theoretical studies reveal a reaction mechanism with nucleophilic addition followed by a swift proton transfer-induced elimination reaction.

SUBMITTER: Guo Y

PROVIDER: S-EPMC8514480 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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Efficient synthesis of primary and secondary amides via reacting esters with alkali metal amidoboranes.

Guo Yu Y Wang Ruo-Ya RY Kang Jia-Xin JX Ma Yan-Na YN Xu Cong-Qiao CQ Li Jun J Chen Xuenian X

Nature communications 20211013 1

Amides are one of the most important organic compounds that are widely applied in medicine, biochemistry, and materials science. To find an efficient synthetic method of amides is a challenge for organic chemistry. We report here a facile synthesis method of primary and secondary amides through a direct amidation of esters with sodium amidoboranes (NaNHRBH<sub>3</sub>, R = H, Me), at room temperature without using catalysts and other reagents. This process is rapid and chemoselective, and featur ...[more]

PMID: 34645807

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