Abstract
Alkylamines are important motifs in pharmaceutical and material sciences. The existing reports of C-H amination are limited to ammonia, diazo and azide nitrogen sources. This work describes a rapid construction of C-N bonds from accessible nitroarene and alkane feedstock under decatungstate catalysis. A variety of C-H precursors including gaseous, linear, cyclic and benzylic hydrocarbons could adopt this protocol to afford the corresponding alkylamines in high efficiency.
References
Nugent TC. Chiral Amine Synthesis: Methods, Developments and Applications. Weinheim: Wiley-VCH, 2010
Blakemore DC, Castro L, Churcher I, Rees DC, Thomas AW, Wilson DM, Wood A. Nat Chem, 2018, 10: 383–394
Cushnie TPT, Cushnie B, Lamb AJ. Int J Antimicrob Agents, 2014, 44: 377–386
Kittakoop P, Mahidol C, Ruchirawat S. Curr Top Med Chem, 2013, 14: 239–252
Banks WA. BMC Neurol, 2009, 9: S3
Mayol-Llinàs J, Farnaby W, Nelson A. Chem Commun, 2017, 53: 12345–12348
Yu LF, Zhang HK, Caldarone BJ, Eaton JB, Lukas RJ, Kozikowski AP. J Med Chem, 2014, 57: 8204–8223
Roughley SD, Jordan AM. J Med Chem, 2011, 54: 3451–3479
Park Y, Kim Y, Chang S. Chem Rev, 2017, 117: 9247–9301
Trowbridge A, Walton SM, Gaunt MJ. Chem Rev, 2020, 120: 2613–2692
Yang Y, Shi SL, Niu D, Liu P, Buchwald SL. Science, 2015, 349: 62–66
Kalck P, Urrutigoïty M. Chem Rev, 2018, 118: 3833–3861
Muñiz K. Acc Chem Res, 2018, 51: 1507–1519
Yang Q, Wang Q, Yu Z. Chem Soc Rev, 2015, 44: 2305–2329
Irrgang T, Kempe R. Chem Rev, 2019, 119: 2524–2549
Scammells PJ. Substitution on the amine nitrogen (update 2013). In: Banert K, Drabowicz J, Oestreich M, Plietker BJ, Ramsden C, Schaumann E, Stoltz BM, Weinreb SM, Eds. Science of Synthesis Knowledge Updates. Stuttgart: Thieme Publishing Group, 2013. 427–461
Salvatore RN, Yoon CH, Jung KW. Tetrahedron, 2001, 57: 7785–7811
Laudadio G, Deng Y, van der Wal K, Ravelli D, Nuño M, Fagnoni M, Guthrie D, Sun Y, Noël T. Science, 2020, 369: 92–96
Li Y, Lei M, Gong L. Nat Catal, 2019, 2: 1016–1026
Fu J, Ren Z, Bacsa J, Musaev DG, Davies HML. Nature, 2018, 564: 395–399
Tran BL, Li B, Driess M, Hartwig JF. J Am Chem Soc, 2014, 136: 2555–2563
Brunard E, Boquet V, van Elslande E, Saget T, Dauban P. J Am Chem Soc, 2021, 143: 6407–6412
Hartwig JF. J Am Chem Soc, 2016, 138: 2–24
Cook AK, Schimler SD, Matzger AJ, Sanford MS. Science, 2016, 351: 1421–1424
Smith KT, Berritt S, González-Moreiras M, Ahn S, Smith III MR, Baik MH, Mindiola DJ. Science, 2016, 351: 1424–1427
Michos D, Sassano CA, Krajnik P, Crabtree RH. Angew Chem Int Ed, 1993, 32: 1491–1492
Bettinger HF, Filthaus M, Bornemann H, Oppel IM. Angew Chem Int Ed, 2008, 47: 4744–4747
Hu A, Guo JJ, Pan H, Zuo Z. Science, 2018, 361: 668–672
Gunsalus NJ, Park SH, Hashiguchi BG, Koppaka A, Smith SJ, Ess DH, Periana RA. Organometallics, 2019, 38: 2319–2322
Lee J, Jin S, Kim D, Hong SH, Chang S. J Am Chem Soc, 2021, 143: 5191–5200
Gui J, Pan CM, Jin Y, Qin T, Lo JC, Lee BJ, Spergel SH, Mertzman ME, Pitts WJ, La Cruz TE, Schmidt MA, Darvatkar N, Natarajan SR, Baran PS. Science, 2015, 348: 886–891
Xiao J, He Y, Ye F, Zhu S. Chem, 2018, 4: 1645–1657
Deng G, Chen W, Li CJ. Adv Synth Catal, 2009, 351: 353–356
Cheung CW, Hu X. Nat Commun, 2016, 7: 12494
Rauser M, Eckert R, Gerbershagen M, Niggemann M. Angew Chem Int Ed, 2019, 58: 6713–6717
Li G, Qin Z, Radosevich AT. J Am Chem Soc, 2020, 142: 16205–16210
Waele VD, Poizat O, Fagnoni M, Bagno A, Ravelli D. ACS Catal, 2016, 6: 7174–7182
Wu W, Fu Z, Tang S, Zou S, Wen X, Meng Y, Sun S, Deng J, Liu Y, Yin D. Appl Catal B-Environ, 2015, 164: 113–119
Schultz DM, Lévesque F, DiRocco DA, Reibarkh M, Ji Y, Joyce LA, Dropinski JF, Sheng H, Sherry BD, Davies IW. Angew Chem Int Ed, 2017, 56: 15274–15278
Laudadio G, Govaerts S, Wang Y, Ravelli D, Koolman HF, Fagnoni M, Djuric SW, Noël T. Angew Chem Int Ed, 2018, 57: 4078–4082
Ioffe SL, Tartakovskii VA, Novikov SS. Russ Chem Rev, 1966, 35: 19–32
Simmons EM, Hartwig JF. Angew Chem Int Ed, 2012, 51: 3066–3072
Tzirakis MD, Lykakis IN, Orfanopoulos M. Chem Soc Rev, 2009, 38: 2609–2621
Nielsen CDT, Burés J. Chem Sci, 2019, 10: 348–353
Perry IB, Brewer TF, Sarver PJ, Schultz DM, DiRocco DA, MacMillan DWC. Nature, 2018, 560: 70–75
Meisel D, Neta P. J Am Chem Soc, 1975, 97: 5198–5203
Chen JR, Yan DM, Wei Q, Xiao WJ. ChemPhotoChem, 2017, 1: 148–158
Yan DM, Xiao C, Chen JR. Chem, 2018, 4: 2496–2498
Chen Y, Lu LQ, Yu DG, Zhu CJ, Xiao WJ. Sci China Chem, 2019, 62: 24–57
Acknowledgements
This work was supported by the National Natural Science Foundation of China (21772085, 21971107, 2201101) and China Postdoctoral Science Foundation (2021T140309, 2021M691511).
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Wang, Q., Ni, S., Wang, X. et al. Visible-light-mediated tungsten-catalyzed C-H amination of unactivated alkanes with nitroarenes. Sci. China Chem. 65, 678–685 (2022). https://doi.org/10.1007/s11426-021-1170-2
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DOI: https://doi.org/10.1007/s11426-021-1170-2