Alkyl Halides as Substrates for Photocatalytic Minisci-Type C–H Alkylation of Hetarenes

Dedicated to Professor Daniel Gryko on the occasion of his 50^th birthday

Abstract

Alkyl halides are readily available starting materials for various synthetic transformations, including Minisci-type C–H functionalizations of hetarenes. The existing methods, however, often require harsh reaction conditions, such as the use of acids, sacrificial electron donors, or radical precursors in excess amounts. Here, we outline recent developments in this field and we highlight our group̓s efforts to achieve fully catalytic photoredox Minisci-type alkylations supported by noncovalent interactions under mild aqueous conditions.

Key words

C–H functionalization - Minisci reaction - alkyl bromides - hetarenes - photoredox catalysis - alkylation

Publication History

Received: 11 February 2021

Accepted after revision: 02 March 2021

Accepted Manuscript online:
02 March 2021

Article published online:
16 March 2021

• References

• 1 Ritchie TJ, Macdonald SJ. F, Young RJ, Pickett SD. Drug Discovery Today 2011; 16: 164
• 2 Snyder SA. Angew. Chem. Int. Ed. 2012; 51: 1307
• 3 Minisci F, Bernardi R, Bertini F, Galli R, Perchinummo M. Tetrahedron 1971; 27: 3575
• 4 Abramovitch RA, Saha JG. J. Chem. Soc. 1964; 2175
• 5 Lynch BM, Chang HS. Tetrahedron Lett. 1964; 5: 2965
• 6 Minisci F, Galli R, Cecere M, Malatesta V, Caronna T. Tetrahedron Lett. 1968; 9: 5609
• 7 Minisci F, Vismara E, Fontana F. Heterocycles 1989; 28: 489
• 8 Tauber J, Imbri D, Opatz T. Molecules 2014; 19: 16190
• 9 Wang Q.-Q, Xu K, Jiang Y.-Y, Liu Y.-G, Sun B.-G, Zeng C.-C. Org. Lett. 2017; 19: 5517
• 10 Yan H, Hou Z.-W, Xu H.-C. Angew. Chem. Int. Ed. 2019; 58: 4592
• 11 O’Brien AG, Maruyama A, Inokuma Y, Fujita M, Baran PS, Blackmond DG. Angew. Chem. Int. Ed. 2014; 53: 11868
• 12 Garza-Sanchez RA, Tlahuext-Aca A, Tavakoli G, Glorius F. ACS Catal. 2017; 7: 4057
• 13 Candish L, Freitag M, Gensch T, Glorius F. Chem. Sci. 2017; 8: 3618
• 14 Duncton MA. J. Med. Chem. Commun. 2011; 2: 1135
• 15 Ye S, Xiang T, Li X, Wu J. Org. Chem. Front. 2019; 6: 2183
• 16 Lekkala R, Lekkala R, Moku B, Rakesh KP, Qin H.-L. Eur. J. Org. Chem. 2019; 2769
• 17 Cybularczyk-Cecotka M, Szczepanik J, Giedyk M. Nat. Catal. 2020; 3: 872
• 18 Minisci F, Vismara E, Fontana F, Morini G, Serravalle M, Giordano C. J. Org. Chem. 1986; 51: 4411
• 19 Fontana F, Minisci F, Vismara E. Tetrahedron Lett. 1988; 29: 1975
• 20 Ren P, Salihu I, Scopelliti R, Hu X. Org. Lett. 2012; 14: 1748
• 21 Wu X, See JW. T, Xu K, Hirao H, Roger J, Hierso J.-C, Zhou J. Angew. Chem. Int. Ed. 2014; 53: 13573
• 22 McCallum T, Barriault L. Chem. Sci. 2016; 7: 4754
• 23 Nuhant P, Oderinde MS, Genovino J, Juneau A, Gagné Y, Allais C, Chinigo GM, Choi C, Sach NW, Bernier L, Fobian YM, Bundesmann MW, Khunte B, Frenette M, Fadeyi OO. Angew. Chem. Int. Ed. 2017; 56: 15309
• 24 Herrick RS, Herrinton TR, Walker HW, Brown TL. Organometallics 1985; 4: 42
• 25 Bissonnette NB, Boyd MJ, May GD, Giroux S, Nuhant P. J. Org. Chem. 2018; 83: 10933
• 26 Dong J, Lyu X, Wang Z, Wang X, Song H, Liu Y, Wang Q. Chem. Sci. 2019; 10: 976
• 27 Chang R, Fang J, Chen J.-Q, Liu D, Xu G.-Q, Xu P.-F. ACS Omega 2019; 4: 14021
• 28 Perkins JJ, Schubert JW, Streckfuss EC, Balsells J, ElMarrouni A. Eur. J. Org. Chem. 2020; 1515
• 29 Crisenza GE. M, Mazzarella D, Melchiorre P. J. Am. Chem. Soc. 2020; 142: 5461
• 30 Jung S, Shin S, Park S, Hong S. J. Am. Chem. Soc. 2020; 142: 11370
• 31 Kerzig C, Goez M. Chem. Sci. 2016; 7: 3862
• 32 Lipshutz BH, Isley NA, Fennewald JC, Slack ED. Angew. Chem. Int. Ed. 2013; 52: 10952
• 33 Giedyk M, Narobe R, Weiß S, Touraud D, Kunz W, König B. Nat. Catal. 2020; 3: 40
• 34 Santos MS, Cybularczyk-Cecotka M, König B, Giedyk M. Chem. Eur. J. 2020; 26: 15323