Photoredox-Catalyzed α-Aminoalkylcarboxylation of Allenes with CO2

Hyungwoo Hahm; Doohyun Baek; Dowon Kim; Seongwook Park; Jeong Yup Ryoo; Sukwon Hong

doi:10.1021/acs.orglett.1c01011

Photoredox-Catalyzed α-Aminoalkylcarboxylation of Allenes with CO₂

Org Lett. 2021 May 21;23(10):3879-3884. doi: 10.1021/acs.orglett.1c01011. Epub 2021 Apr 29.

Authors

Hyungwoo Hahm¹, Doohyun Baek¹, Dowon Kim¹, Seongwook Park¹, Jeong Yup Ryoo¹, Sukwon Hong^{1

2}

Affiliations

¹ Department of Chemistry, Gwangju Institute of Science and Technology, 123 Cheomdan-gwagiro, Buk-gu, Gwangju 61005, Republic of Korea.
² School of Materials Science and Engineering, Gwangju Institute of Science and Technology, 123 Cheomdan-gwagiro, Buk-gu, Gwangju 61005, Republic of Korea.

PMID: 33913718
DOI: 10.1021/acs.orglett.1c01011

Abstract

The photoredox-catalyzed α-aminoalkylcarboxylation of aryl allenes with CO₂ and N,N-dimethylanilines is reported for the first time (26 examples, up to 96% yield). In the case of electron-deficient allenes, good regioselectivity was observed (up to 94:6), exclusively generating kinetic products over thermodynamic products. This protocol is a novel synthetic method for highly functionalized β,γ-unsaturated γ-aminobutyric esters.