Enantioselective intermolecular [2 + 2] photocycloadditions of vinylazaarenes with triplet-state electron-deficient olefins

doi:10.1016/S1872-2067(22)64156-1

Abstract

Abstract:

The development of catalytic asymmetric radical reactions is an attractive but formidable task. The high reactivity of radicals enables the use of readily accessible feedstocks and mild reaction conditions, but it leads to substantial difficulty for chiral catalysts to provide sufficient enantiocontrol. Moreover, a racemic background process is often inevitable, further deteriorating enantioselectivity. In this regard, an effective protocol has been established for enantioselective intermolecular [2 + 2] photocycloadditions to overcome the challenges, which is capitalising on the ground-state preassociations of chiral catalysts with photoactivated substrates. Here, we report the viability of substrate-differentiating synergistic catalysis for this important reaction. In this new platform, energy transfer occurs between DPZ as a photosensitizer and enones or (E)-2-substituted vinylazaarenes for producing triplet-state species, and chiral phosphoric acid interacts with ground-state 2-vinylazaarenes via hydrogen bonding for subsequent enantiofacial cycloaddition. Although all active species are dispersed in the reaction system, valuable enantioenriched mono- and di-azaarene-functionalized cyclobutanes are obtained efficiently and selectively. In addition to constructing all-carbon quaternary stereocentres, flexible modulation of azaaryl groups and other substituents on the cyclobutane ring is also operative.

Key words: Asymmetric photocatalysis, Cooperative catalysis, Energy transfer, [2 + 2] photocycloaddition, Azaarenes

Dong Tian, Xin Sun, Shanshan Cao, Er-Meng Wang, Yanli Yin, Xiaowei Zhao, Zhiyong Jiang. Enantioselective intermolecular [2 + 2] photocycloadditions of vinylazaarenes with triplet-state electron-deficient olefins[J]. Chinese Journal of Catalysis, 2022, 43(10): 2732-2742.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(22)64156-1

https://www.cjcatal.com/EN/Y2022/V43/I10/2732

Figures/Tables 7

Fig. 1. Catalytic asymmetric intermolecular [2 + 2] photocycloadditions. (a) Common strategy; (b) Yoon’s strategy; (c) New reaction mode in the dispersed reaction system; (d) Summary of this work. Fg = functional group; Cat* = chiral catalyst; *[Ir*] = photoactivated chiral Ir complex; EnT = energy transfer; ee = enantiomeric excess; EWG = electron-withdrawing group; CPA = chiral phosphoric acid; DPZ = dicyanopyrazine-derived chromophere; 3DPZ* = triplet-state DPZ.

Fig. 2. Survey of CPAs and photosensitizers. Yield of isolated product. Dr was determined by crude 1H NMR analysis. ee of the major diastereomer was determined by HPLC analysis on a chiral stationary phase. MS = molecular sieve. a fac-Ir(ppy)3 instead of DPZ was used. b Rose Bengal instead of DPZ was used. ppy = 2-(2-pyridyl)phenyl.

Table 1 Substrate scope of enantioselective [2 + 2] photocycloadditions of enones with vinylazaarenes and alkenylazaarenes a.

Table 2 Substrate scope of enantioselective [2 + 2] photocycloadditions of (E)-2-substituted vinylazaarenes with vinylazaarenesa.

Fig. 3. Synthetic applications.

Fig. 4. Mechanistic studies. (a) Relationship between ee values of C1 and 3; (b) Stern-Volmer quenching experiments (?196.15 °C); (c) Effect of pyrene; (d) Reaction of (Z)-2-styrylpyridine with 2-(but-1-en-2-yl)-4-methylquinoline.

Fig. 5. DFT calculations of the radical addition of vinylazaarene 2 and the radical enone r-1 or (E)-2-substituted vinylazaarene r-N. Computational method: B3LYP-D3/6-31G(d,p)//SMD/M062X/6-31+G(d,p) level in solvent phase.

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