Photoredox-catalyzed C–C bond cleavage of cyclopropanes for the formation of C(sp3)–heteroatom bonds

Liang Ge, Chi Zhang, Chengkai Pan, Ding-Xing Wang, Dong-Ying Liu, Zhi-Qiang Li, Pingkang Shen, Lifang Tian and Chao Feng ()
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Liang Ge: Nanjing Tech University
Chi Zhang: Nanjing Tech University
Chengkai Pan: Nanjing Tech University
Ding-Xing Wang: Nanjing Tech University
Dong-Ying Liu: Nanjing Tech University
Zhi-Qiang Li: Nanjing Tech University
Pingkang Shen: Nanjing Tech University
Lifang Tian: Nanjing Tech University
Chao Feng: Nanjing Tech University

Nature Communications, 2022, vol. 13, issue 1, 1-13

Abstract: Abstract Sterically congested C–O and C–N bonds are ubiquitous in natural products, pharmaceuticals, and bioactive compounds. However, the development of a general method for the efficient construction of those sterically demanding covalent bonds still remains a formidable challenge. Herein, a photoredox-driven ring-opening C(sp3)–heteroatom bond formation of arylcyclopropanes is presented, which enables the construction of structurally diversified while sterically congested dialkyl ether, alkyl ester, alcohol, amine, chloride/fluoride, azide and also thiocyanate derivatives. The selective single electron oxidation of aryl motif associated with the thermodynamic driving force from ring strain-release is the key for this transformation. By this synergistic activation mode, C–C bond cleavage of otherwise inert cyclopropane framework is successfully unlocked. Further mechanistic and computational studies disclose a complete stereoinversion upon nucleophilic attack, thus proving a concerted SN2-type ring-opening functionalization manifold, while the regioselectivity is subjected to an orbital control scenario.

Date: 2022
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DOI: 10.1038/s41467-022-33602-4

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