Recent Catalytic Routes to 3-Azabicyclo[3.1.0]hexane Derivatives

Мұқаба

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
Рұқсат жабық Тек жазылушылар үшін

Аннотация

The review summarizes recent achievements in the synthesis of 3-azabicyclo[3.1.0]hexanes (3-ABH). These heterocyclic systems are ubiquitous in the structure of molecules that can act on a variety of biological targets and are actively used in drug design. Classification and analysis of the modern approaches to 3-ABHs based on the use of transition metal complexes are carried out, and the mechanisms of the key processes are considered. The presented reactions include the assembly of 3-ABH by annulation of three- or five-membered rings as well as numerous one-step syntheses from acyclic precursors via tandem cyclizations.

Толық мәтін

Рұқсат жабық

Авторлар туралы

K. Barashkova

Chemistry Department, M. V. Lomonosov Moscow State University

Хат алмасуға жауапты Автор.
Email: kotovshchikov@org.chem.msu.ru
ORCID iD: 0000-0003-2103-5985
Ресей, Moscow

G. Latyshev

Chemistry Department, M. V. Lomonosov Moscow State University

Email: kotovshchikov@org.chem.msu.ru
Ресей, Moscow

Y. Kotovshchikov

Chemistry Department, M. V. Lomonosov Moscow State University

Email: kotovshchikov@org.chem.msu.ru
Ресей, Moscow

N. Lukashev

Chemistry Department, M. V. Lomonosov Moscow State University

Email: kotovshchikov@org.chem.msu.ru
Ресей, Moscow

I. Beletskaya

Chemistry Department, M. V. Lomonosov Moscow State University

Email: kotovshchikov@org.chem.msu.ru
Ресей, Moscow

Әдебиет тізімі

  1. Stauffacher D., Niklaus P., Tscherter H., Weber H.P., Hofmann A. Tetrahedron. 1969, 25, 5879–5887. doi: 10.1016/S0040-4020(01)83095-7
  2. Gomi S., Ikeda D., Nakamura H., Naganawa H., Yamashita F., Hotta K., Kondo S., Okami Y., Umezawa H., Iitaka Y. J. Antibiot. 1984, 37, 1491–1494. doi: 10.7164/antibiotics.37.1491
  3. Takahashi I., Takahashi K.-I., Ichimura M., Morimoto M., Asano K., Kawamoto I., Tomita F., Nakano H. J. Antibiot. 1988, 41, 1915–1917. doi: 10.7164/antibiotics.41.1915
  4. Li L.H., Kelly R.C., Warpehoski M.A., McGovren J.P., Gebhard I., DeKoning T.F. Invest. New Drugs. 1991, 9, 137–148. doi: 10.1007/BF00175081
  5. Gootz T.D., Zaniewski R., Haskell S., Schmieder B., Tankovic J., Girard D., Courvalin P., Polzer R.J. Antimicrob. Agents Chemother. 1996, 40, 2691–2697. doi: 10.1128/AAC.40.12.2691
  6. Epstein J.W., Brabander H.J., Fanshawe W.J., Hofmann C.M., McKenzie T.C., Safir S.R., Osterberg A.C., Cosulich D.B., Lovell F.M. J. Med. Chem. 1981, 24, 481–490. doi: 10.1021/jm00137a002
  7. Bymaster F.P., Golembiowska K., Kowalska M., Choi Y.K., Tarazi F.I. Synapse. 2012, 66, 522–532. doi: 10.1002/syn.21538
  8. Skolnick P., Popik P., Janowsky A., Beer B., Lippa A.S. Eur. J. Pharmacol. 2003, 461, 99–104. doi: 10.1016/S0014-2999(03)01310-4
  9. Venkatraman S., Bogen S.L., Arasappan A., Bennett F., Chen K., Jao E., Liu Y.-T., Lovey R., Hendrata S., Huang Y., Pan W., Parekh T., Pinto P., Popov V., Pike R., Ruan S., Santhanam B., Vibulbhan B., Wu W., Yang W., Kong J., Liang X., Wong J., Liu R., Butkiewicz N., Chase R., Hart A., Agrawal S., Ingravallo P., Pichardo J., Kong R., Baroudy B., Malcolm B., Guo Z., Prongay A., Madison V., Broske L., Cui X., Cheng K.-C., Hsieh Y., Brisson J.-M., Prelusky D., Korfmacher W., White R., Bogdanowich-Knipp S., Pavlovsky A., Bradley P., Saksena A.K., Ganguly A., Piwinski J., Girijavallabhan V., Njoroge F.G. J. Med. Chem. 2006, 49, 6074–6086. doi: 10.1021/jm060325b
  10. Reesink H., Bergmann J., De Bruijne J., Weegink C., Van Lier J., Van Vliet A., Keung A., Li J., O’Mara E., Treitel M., Hughes E., Janssen H., De Knegt R. J. Hepatol. 2009, 50, S35–S36. doi: 10.1016/S0168-8278(09)60088-X
  11. Hashemian S.M.R., Sheida A., Taghizadieh M., Memar M.Y., Hamblin M.R., Bannazadeh Baghi H., Sadri Nahand J., Asemi Z., Mirzaei H. Biomed. Pharmacother. 2023, 162, 114367. doi: 10.1016/j.biopha.2023.114367
  12. Fensome A., Ambler C.M., Arnold E., Banker M.E., Clark J.D., Dowty M.E., Efremov I.V., Flick A., Gerstenberger B.S., Gifford R.S., Gopalsamy A., Hegen M., Jussif J., Limburg D.C., Lin T.H., Pierce B.S., Sharma R., Trujillo J.I., Vajdos F.F., Vincent F., Wan Z.-K., Xing L., Yang X., Yang X. Bioorg. Med. Chem. 2020, 28, 115481. doi: 10.1016/j.bmc.2020.115481
  13. Zhang L., Butler C.R., Maresca K.P., Takano A., Nag S., Jia Z., Arakawa R., Piro J.R., Samad T., Smith D.L., Nason D.M., O’Neil S., McAllister L., Schildknegt K., Trapa P., McCarthy T.J., Villalobos A., Halldin C. J. Med. Chem. 2019, 62, 8532–8543. doi: 10.1021/acs.jmedchem.9b00847
  14. Patel S., Meilandt W.J., Erickson R.I., Chen J., Deshmukh G., Estrada A.A., Fuji R.N., Gibbons P., Gustafson A., Harris S.F., Imperio J., Liu W., Liu X., Liu Y., Lyssikatos J.P., Ma C., Yin J., Lewcock J.W., Siu M. J. Med. Chem. 2017, 60, 8083–8102. doi: 10.1021/acs.jmedchem.7b00843
  15. Micheli F., Arista L., Bonanomi G., Blaney F.E., Braggio S., Capelli A.M., Checchia A., Damiani F., Di-Fabio R., Fontana S., Gentile G., Griffante C., Hamprecht D., Marchioro C., Mugnaini M., Piner J., Ratti E., Tedesco G., Tarsi L., Terreni S., Worby A., Ashby C.R., Heidbreder C. J. Med. Chem. 2010, 53, 374–391. doi: 10.1021/jm901319p
  16. Kuttruff C.A., Ferrara M., Bretschneider T., Hoerer S., Handschuh S., Nosse B., Romig H., Nicklin P., Roth G.J. ACS Med. Chem. Lett. 2017, 8, 1252–1257. doi: 10.1021/acsmedchemlett.7b00312
  17. Zhang S., Li L., Meng G., Zhang X., Hou L., Hua X., Wang M. Sustainability. 2021, 13, 6712. doi: 10.3390/su13126712
  18. Krow G.R., Cannon K.C. Org. Prep. Proced. Int. 2000, 32, 103–122. doi: 10.1080/00304940009356278
  19. Ershov O.V., Bardasov I.N. Chem. Heterocycl. Compd. 2016, 52, 447–449. doi: 10.1007/s10593-016-1910-y
  20. Allouche E.M.D., Charette A.B. Synthesis. 2019, 51, 3947–3963. doi: 10.1055/s-0037-1611915
  21. Dorel R., Echavarren A.M. J. Org. Chem. 2015, 80, 7321–7332. doi: 10.1021/acs.joc.5b01106
  22. Giovanardi G., Balestri D., Secchi A., Cera G. Org. Biomol. Chem. 2022, 20, 6464–6472. doi: 10.1039/D2OB01074G
  23. Kale B.S., Lee H., Liu R. Adv. Synth. Catal. 2017, 359, 402–409. doi: 10.1002/adsc.201600980
  24. Wang Y.-J., Li X.-X., Chen Z. J. Org. Chem. 2020, 85, 7694–7703. doi: 10.1021/acs.joc.0c00146
  25. Yang J.-M., Zhao Y.-T., Li Z.-Q., Gu X.-S., Zhu S.-F., Zhou Q.-L. ACS Catal. 2018, 8, 7351–7355. doi: 10.1021/acscatal.8b02052
  26. Yang J.-M., Li Z.-Q., Li M.-L., He Q., Zhu S.-F., Zhou Q.-L. J. Am. Chem. Soc. 2017, 139, 3784–3789. doi: 10.1021/jacs.6b13168
  27. Zeineddine A., Rekhroukh F., Sosa Carrizo E.D., Mallet-Ladeira S., Miqueu K., Amgoune A., Bourissou D. Angew. Chem. Int. Ed. 2018, 57, 1306–1310. doi: 10.1002/anie.201711647
  28. Wang G., Wang Y., Li Z., Li H., Yu M., Pang M., Zhao X. Org. Lett. 2022, 24, 9425–9430. doi: 10.1021/acs.orglett.2c03812
  29. Sánchez-Cantalejo F., Priest J.D., Davies P.W. Chem. Eur. J. 2018, 24, 17215–17219. doi: 10.1002/chem.201804378
  30. Liu J., Zhu L., Wan W., Huang X. Org. Lett. 2020, 22, 3279–3285. doi: 10.1021/acs.orglett.0c01086
  31. Xia J., Liu J., Yu Y., Zhang J., Huang X. Org. Lett. 2022, 24, 4298–4303. doi: 10.1021/acs.orglett.2c01807
  32. Song L., Tian X., Rudolph M., Rominger F., Hashmi A.S.K. Chem. Commun. 2019, 55, 9007–9010. doi: 10.1039/C9CC04027G
  33. Shcherbakov N.V., Dar’in D.V., Kukushkin V.Yu., Dubovtsev A.Yu. J. Org. Chem. 2021, 86, 12964–12972. doi: 10.1021/acs.joc.1c01654
  34. Tian X., Song L., Rudolph M., Rominger F., Oeser T., Hashmi A.S.K. Angew. Chem. Int. Ed. 2019, 58, 3589–3593. doi: 10.1002/anie.201812002
  35. Munakala A., Gollapelli K.K., Nanubolu J.B., Chegondi R. Org. Lett. 2020, 22, 7019–7024. doi: 10.1021/acs.orglett.0c02555
  36. Chen X., Luo Z., Chen Y., Zhang Y. Org. Lett. 2022, 24, 9200–9204. doi: 10.1021/acs.orglett.2c03619
  37. Shen W.-B., Tang X.-T., Zhang T.-T., Lv D.-C., Zhao D., Su T.-F., Meng L. Org. Lett. 2021, 23, 1285–1290. doi: 10.1021/acs.orglett.0c04268
  38. Monnier F., Castillo D., Dérien S., Toupet L., Dixneuf P.H. Angew. Chem. Int. Ed. 2003, 42, 5474–5477. doi: 10.1002/anie.200352477
  39. Monnier F., Vovard-Le Bray C., Castillo D., Aubert V., Dérien S., Dixneuf P.H., Toupet L., Ienco A., Mealli C. J. Am. Chem. Soc. 2007, 129, 6037–6049. doi: 10.1021/ja0700146
  40. Gao M., Gao Q., Hao X., Wu Y., Zhang Q., Liu G., Liu R. Org. Lett. 2020, 22, 1139–1143. doi: 10.1021/acs.orglett.9b04662
  41. Guthertz A., Leutzsch M., Wolf L.M., Gupta P., Rummelt S.M., Goddard R., Farès C., Thiel W., Fürstner A. J. Am. Chem. Soc. 2018, 140, 3156–3169. doi: 10.1021/jacs.8b00665
  42. Peil S., Bistoni G., Goddard R., Fürstner A. J. Am. Chem. Soc. 2020, 142, 18541–18553. doi: 10.1021/jacs.0c07808
  43. Peil S., Guthertz A., Biberger T., Fürstner A. Angew. Chem. Int. Ed. 2019, 58, 8851–8856. doi: 10.1002/anie.201904256
  44. Tan Y., Li S., Song L., Zhang X., Wu Y., Sun J. Angew. Chem. Int. Ed. 2022, 61, e202204319. doi: 10.1002/anie.202204319
  45. Feng J.-J., Zhang J. ACS Catal. 2017, 7, 1533–1542. doi: 10.1021/acscatal.6b03399
  46. Huang J., Hu X., Chen F., Gui J., Zeng W. Org. Biomol. Chem. 2019, 17, 7042–7054. doi: 10.1039/C9OB01028A
  47. Hou S.-H., Yu X., Zhang R., Wagner C., Dong G. J. Am. Chem. Soc. 2022, 144, 22159–22169. doi: 10.1021/jacs.2c09814
  48. Suleymanov A.A., Vasilyev D.V., Novikov V.V., Nelyubina Y.V., Perekalin D.S. Beilstein J. Org. Chem. 2017, 13, 639–643. doi: 10.3762/bjoc.13.62
  49. Herbort J.H., Lalisse R.F., Hadad C.M., Rajan Babu T.V. ACS Catal. 2021, 11, 9605–9617. doi: 10.1021/acscatal.1c02530
  50. Liu W., Tong X. Org. Lett. 2019, 21, 9396–9400. doi: 10.1021/acs.orglett.9b03621
  51. Ghosh N., Maiereanu C., Suffert J., Blond G. Synlett 2017, 28, 451–455. doi: 10.1055/s-0036-1588658
  52. Sun D., Zhou B., Liu L., Chen X., Hou H., Han Y., Yan C., Shi Y., Zhu S. Org. Lett. 2023, 25, 4677–4681. doi: 10.1021/acs.orglett.3c01551
  53. Marco-Martínez J., López-Carrillo V., Buñuel E., Simancas R., Cárdenas D.J. J. Am. Chem. Soc. 2007, 129, 1874–1875. doi: 10.1021/ja0685598
  54. Mekareeya A., Walker P.R., Couce-Rios A., Campbell C.D., Steven A., Paton R.S., Anderson E.A. J. Am. Chem. Soc. 2017, 139, 10104–10114. doi: 10.1021/jacs.7b05436
  55. Gao N., Banwell M.G., Willis A.C. Org. Lett. 2017, 19, 162–165. doi: 10.1021/acs.orglett.6b03465
  56. Trost B.M., Lautens M., Chan C., Jebaratnam D.J., Mueller T. J. Am. Chem. Soc. 1991, 113, 636–644. doi: 10.1021/ja00002a036
  57. Chaki B.M., Takenaka K., Zhu L., Tsujihara T., Takizawa S., Sasai H. Adv. Synth. Catal. 2020, 362, 1537–1547. doi: 10.1002/adsc.202000044
  58. Grigg R., Rasul R., Redpath J., Wilson D. Tetrahedron Lett. 1996, 37, 4609–4612. doi: 10.1016/0040-4039(96)00889-1
  59. Oppolzer W., Pimm A., Stammen B., Hume W.E. Helv. Chim. Acta. 1997, 80, 623–639. doi: 10.1002/hlca.19970800302
  60. Böhmer J., Grigg R., Marchbank J.D. Chem. Commun. 2002, 768–769. doi: 10.1039/b110890e
  61. Huang X., Nguyen M.H., Pu M., Zhang L., Chi Y.R., Wu Y.-D., Zhou J.S. Angew. Chem. Int. Ed. 2020, 59, 10814–10818. doi: 10.1002/anie.202000859
  62. Kleban I., Krokhmaliuk Y., Reut S., Shuvakin S., Pen-dyukh V.V., Khyzhan O.I., Yarmoliuk D.S., Tymtsunik A.V., Rassukana Y.V., Grygorenko O.O. Eur. J. Org. Chem. 2021, 2021, 6551–6560. doi: 10.1002/ejoc.202000977
  63. Harris M.R., Li Q., Lian Y., Xiao J., Londregan A.T. Org. Lett. 2017, 19, 2450–2453. doi: 10.1021/acs.orglett.7b01097
  64. Chen P., Zhu C., Zhu R., Lin Z., Wu W., Jiang H. Org. Biomol. Chem. 2017, 15, 1228–1235. doi: 10.1039/C6OB02137A
  65. Doyle M.P., Loh K.-L., DeVries K.M., Chinn M.S. Tetrahedron Lett. 1987, 28, 833–836. doi: 10.1016/S0040-4039(01)81001-7
  66. Haddad N., Galili N. Tetrahedron: Asymmetry. 1997, 8, 3367–3370. doi: 10.1016/S0957-4166(97)00463-1
  67. Gross Z., Galili N., Simkhovich L. Tetrahedron Lett. 1999, 40, 1571–1574. doi: 10.1016/S0040-4039(98)02647-1
  68. Muthusamy S., Gunanathan C. Synlett. 2003, 1599–1602. doi: 10.1055/s-2003-40996
  69. Ueda J., Harada S., Kanda A., Nakayama H., Nemoto T. J. Org. Chem. 2020, 85, 10934–10950. doi: 10.1021/acs.joc.0c01580
  70. Mandour H.S.A., Chanthamath S., Shibatomi K., Iwasa S. Adv. Synth. Catal. 2017, 359, 1742–1746. doi: 10.1002/adsc.201601345
  71. Chanthamath S., Mandour H.S.A., Tong T.M.T., Shibatomi K., Iwasa S. Chem. Commun. 2016, 52, 7814–7817. doi: 10.1039/C6CC02498J
  72. Mandour H.S.A., Nakagawa Y., Tone M., Inoue H., Otog N., Fujisawa I., Chanthamath S., Iwasa S. Beilstein J. Org. Chem. 2019, 15, 357–363. doi: 10.3762/bjoc.15.31
  73. Matsuo T., Miyake T., Hirota S. Tetrahedron Lett. 2019, 60, 151226. doi: 10.1016/j.tetlet.2019.151226
  74. Zetzsche L.E., Narayan A.R.H. Nat. Rev. Chem. 2020, 4, 334–346. doi: 10.1038/s41570-020-0191-2
  75. Van Stappen C., Deng Y., Liu Y., Heidari H., Wang J. X., Zhou Y., Ledray A.P., Lu Y. Chem. Rev. 2022, 122, 11974–12045. doi: 10.1021/acs.chemrev.2c00106
  76. Chandgude A.L., Ren X., Fasan R. J. Am. Chem. Soc. 2019, 141, 9145–9150. doi: 10.1021/jacs.9b02700
  77. Ren X., Chandgude A.L., Fasan R. ACS Catal. 2020, 10, 2308–2313. doi: 10.1021/acscatal.9b05383
  78. Darses B., Maldivi P., Philouze C., Dauban P., Poisson J.-F. Org. Lett. 2021, 23, 300–304. doi: 10.1021/acs.orglett.0c03774
  79. Homma H., Harada S., Ito T., Kanda A., Nemoto T. Org. Lett. 2020, 22, 8132–8138. doi: 10.1021/acs.orglett.0c03110
  80. Sontakke G.S., Pal K., Volla C.M.R. J. Org. Chem. 2019, 84, 12198–12208. doi: 10.1021/acs.joc.9b01924
  81. Zhu C.-Z., Wei Y., Shi M. Org. Chem. Front. 2019, 6, 2884–2891. doi: 10.1039/C9QO00714H
  82. Stahl K., Hertzsch W., Musso H. Liebigs Ann. Chem. 1985, 1474–1484. doi: 10.1002/jlac.198519850718
  83. Charette A.B., Wilb N. Synlett. 2002, 176–178. doi: 10.1055/s-2002-19345
  84. Werth J., Uyeda C. Angew. Chem. Int. Ed. 2018, 57, 13902–13906. doi: 10.1002/anie.201807542
  85. Huo H., Gong Y. Org. Biomol. Chem. 2022, 20, 3847–3869. doi: 10.1039/D1OB02450G
  86. Molchanov A.P., Efremova M.M., Kuznetsov M.A. Russ. Chem. Bull. 2022, 71, 620–650. doi: 10.1007/s11172-022-3460-z
  87. Filatov A.S., Knyazev N.A., Molchanov A.P., Panikorovsky T.L., Kostikov R.R., Larina A.G., Boitsov V.M., Stepakov A.V. J. Org. Chem. 2017, 82, 959–975. doi: 10.1021/acs.joc.6b02505
  88. Filatov A.S., Wang S., Khoroshilova O.V., Lozovskiy S.V., Larina A.G., Boitsov V.M., Stepakov A.V. J. Org. Chem. 2019, 84, 7017–7036. doi: 10.1021/acs.joc.9b00753
  89. Shmakov S.V., Latypova D.K., Shmakova T.V., Rubinshtein A.A., Chukin M.V., Zhuravskii S.G., Knyazev N.A., Stepakov A.V., Galagudza M.M., Boitsov V.M. Int. J. Mol. Sci. 2022, 23, 10759. doi: 10.3390/ijms231810759
  90. Deng H., Yang W.-L., Tian F., Tang W., Deng W.-P. Org. Lett. 2018, 20, 4121–4125. doi: 10.1021/acs.orglett.8b01686
  91. Yuan Y., Zheng Z.-J., Ye F., Ma J.-H., Xu Z., Bai X.-F., Li L., Xu L.-W. Org. Chem. Front. 2018, 5, 2759–2764. doi: 10.1039/C8QO00761F
  92. López-Rodríguez A., Domínguez G., Pérez-Castells J. J. Org. Chem. 2019, 84, 924–933. doi: 10.1021/acs.joc.8b02849
  93. Rogge T., Kaplaneris N., Chatani N., Kim J., Chang S., Punji B., Schafer L.L., Musaev D.G., Wencel-Delord J., Roberts C.A., Sarpong R., Wilson Z.E., Brimble M.A., Johansson M.J., Ackermann L. Nat. Rev. Methods Primers. 2021, 1, 43. doi: 10.1038/s43586-021-00041-2
  94. He J., Wasa M., Chan K.S.L., Shao Q., Yu J.-Q. Chem. Rev. 2017, 117, 8754–8786. doi: 10.1021/acs.chemrev.6b00622
  95. Gandeepan P., Müller T., Zell D., Cera G., Warratz S., Ackermann L. Chem. Rev. 2019, 119, 2192–2452. doi: 10.1021/acs.chemrev.8b00507
  96. Nakanishi M., Katayev D., Besnard C., Kündig E.P. Angew. Chem. Int. Ed. 2011, 50, 7438–7441. doi: 10.1002/anie.201102639
  97. Saget T., Cramer N. Angew. Chem. Int. Ed. 2012, 51, 12842–12845. doi: 10.1002/anie.201207959
  98. Pedroni J., Cramer N. Angew. Chem. Int. Ed. 2015, 54, 11826–11829. doi: 10.1002/anie.201505916
  99. Dailler D., Rocaboy R., Baudoin O. Angew. Chem. Int. Ed. 2017, 56, 7218–7222. doi: 10.1002/anie.201703109
  100. Pedroni J., Cramer N. J. Am. Chem. Soc. 2017, 139, 12398–12401. doi: 10.1021/jacs.7b07024
  101. Jerhaoui S., Djukic J.-P., Wencel-Delord J., Colobert F. ACS Catal. 2019, 9, 2532–2542. doi: 10.1021/acscatal.8b04946
  102. He C., Gaunt M.J. Chem. Sci. 2017, 8, 3586–3592. doi: 10.1039/C7SC00468K
  103. Zhuang Z., Yu J.-Q. J. Am. Chem. Soc. 2020, 142, 12015–12019. doi: 10.1021/jacs.0c04801
  104. Barsu N., Bolli S.K., Sundararaju B. Chem. Sci. 2017, 8, 2431–2435. doi: 10.1039/C6SC05026C
  105. Williamson P., Galván A., Gaunt M.J. Chem. Sci. 2017, 8, 2588–2591. doi: 10.1039/C6SC05581H
  106. Barsu N., Kalsi D., Sundararaju B. Catal. Sci. Technol. 2018, 8, 5963–5969. doi: 10.1039/C8CY02060D
  107. Ma S., Gu Z. Angew. Chem. Int. Ed. 2005, 44, 7512–7517. doi: 10.1002/anie.200501298
  108. Clemenceau A., Thesmar P., Gicquel M., Le Flohic A., Baudoin O. J. Am. Chem. Soc. 2020, 142, 15355–15361. doi: 10.1021/jacs.0c05887
  109. Veeranna K.D., Das K.K., Baskaran S. Angew. Chem. Int. Ed. 2017, 56, 16197–16201. doi: 10.1002/anie.201708138
  110. Xu H., Han T., Luo X., Deng W.-P. Chin. J. Chem. 2021, 39, 666–670. doi: 10.1002/cjoc.202000405
  111. Veeranna K.D., Das K.K., Baskaran S. Org. Biomol. Chem. 2021, 19, 4054–4059. doi: 10.1039/D1OB00416F
  112. Veeranna K.D., Das K.K., Baskaran S. Chem. Commun. 2019, 55, 7647–7650. doi: 10.1039/C9CC03647D
  113. Huang F., Wu P., Yu Z. J. Org. Chem. 2020, 85, 4373–4385. doi: 10.1021/acs.joc.0c00093
  114. Toh K.K., Biswas A., Wang Y.-F., Tan Y.Y., Chiba S. J. Am. Chem. Soc. 2014, 136, 6011–6020. doi: 10.1021/ja500382c
  115. Wang Y., Shen S., He C., Zhou Y., Zhang K., Rao B., Han T., Su Y., Duan X.-H., Liu L. Chem. Sci. 2023, 14, 6663–6668. doi: 10.1039/D3SC01752D
  116. Twilton J., Le C., Zhang P., Shaw M.H., Evans R.W., MacMillan D.W.C. Nat. Rev. Chem. 2017, 1, 0052. doi: 10.1038/s41570-017-0052
  117. Chan A.Y., Perry I.B., Bissonnette N.B., Buksh B.F., Edwards G.A., Frye L.I., Garry O.L., Lavagnino M.N., Li B.X., Liang Y., Mao E., Millet A., Oakley J.V., Reed N.L., Sakai H.A., Seath C.P., MacMillan D.W.C. Chem. Rev. 2022, 122, 1485–1542. doi: 10.1021/acs.chemrev.1c00383
  118. Romero N.A., Nicewicz D.A. Chem. Rev. 2016, 116, 10075–10166. doi: 10.1021/acs.chemrev.6b00057
  119. Deng Y., Zhang J., Bankhead B., Markham J.P., Zeller M. Chem. Commun. 2021, 57, 5254–5257. doi: 10.1039/D1CC02016A
  120. Lanzi M., Santacroce V., Balestri D., Marchiò L., Bigi F., Maggi R., Malacria M., Maestri G. Angew. Chem. Int. Ed. 2019, 58, 6703–6707. doi: 10.1002/anie.201902837
  121. Ide K., Furuta M., Tokuyama H. Org. Biomol. Chem. 2021, 19, 9172–9176. doi: 10.1039/D1OB01733K
  122. Lu Y., Chen C., Zhu H., Luo Z., Zhang Y. Green Chem. 2022, 24, 8021–8028. doi: 10.1039/D2GC02058K
  123. Piou T., Rovis T. J. Am. Chem. Soc. 2014, 136, 11292–11295. doi: 10.1021/ja506579t
  124. Lahtigui O., Forster D., Duchemin C., Cramer N. ACS Catal. 2022, 12, 6209–6215. doi: 10.1021/acscatal.2c01827

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