Enantioselective carbenoid insertion into C(sp3)–H bonds

J. V. Santiago and A. H. L. Machado
Beilstein J. Org. Chem. 2016, 12, 882–902. https://doi.org/10.3762/bjoc.12.87

Cite the Following Article

Enantioselective carbenoid insertion into C(sp3)–H bonds
J. V. Santiago and A. H. L. Machado
Beilstein J. Org. Chem. 2016, 12, 882–902. https://doi.org/10.3762/bjoc.12.87

How to Cite

Santiago, J. V.; Machado, A. H. L. Beilstein J. Org. Chem. 2016, 12, 882–902. doi:10.3762/bjoc.12.87

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 97.8 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Li, X.; Yue, S.-H.; Tan, Z.-Y.; Liu, S.-B.; Luo, D.-X.; Zhou, Y.-J.; Liang, X.-W. Catalytic asymmetric carbenoid α-C-H insertion of ether. RSC advances 2024, 14, 15167–15177. doi:10.1039/d4ra02206h
  • Wackelin, D. J.; Mao, R.; Sicinski, K. M.; Zhao, Y.; Das, A.; Chen, K.; Arnold, F. H. Enzymatic Assembly of Diverse Lactone Structures: An Intramolecular C-H Functionalization Strategy. Journal of the American Chemical Society 2024, 146, 1580–1587. doi:10.1021/jacs.3c11722
  • Ghosh, T. Asymmetric Nickel-Catalyzed Reactions. Comprehensive Chirality; Elsevier, 2024; pp 234–353. doi:10.1016/b978-0-32-390644-9.00118-9
  • Yan, M.; Xiao, L.; Xiong, J.; Jin, L.; Stephan, D. W.; Guo, J. Borane catalyzed transesterification of tert-butyl esters using α-aryl α-diazoesters. Organic & biomolecular chemistry 2023, 21, 8279–8283. doi:10.1039/d3ob01548c
  • Santiago, J. V.; Orłowska, K.; Ociepa, M.; Gryko, D. Aryl versus Alkyl Redox-Active Diazoacetates ─ Light-Induced C-H Insertion or 1,2-Rearrangement. Organic letters 2023, 25, 6267–6271. doi:10.1021/acs.orglett.3c02055
  • Sen, S.; Maiti, D.; Singh, S.; Gremaud, L. A Combination of Computational and Experimental Studies to Correlate Electronic Structure and Reactivity of Donor–Acceptor Singlet Carbenes. Synlett 2023, 35, 319–324. doi:10.1055/a-2153-6819
  • Melen, R. L.; Pramanik, M. Activation of Diazo Compounds by Fluorinated Triarylborane Catalysts. Synthesis 2023, 55, 3906–3918. doi:10.1055/a-2118-3046
  • Xiao, L.; Jin, L.; Zhao, Y.; Guo, J.; Stephan, D. W. B(C6F5)3-catalyzed cyclopropanation of 3-alkenyl-oxindoles with diazomethanes. Chemical communications (Cambridge, England) 2023, 59, 1833–1836. doi:10.1039/d2cc06744g
  • Shibata, T.; Pan, S. doi:10.1002/9783527834242.chf0128
  • Zhu, S.; Qin, J.; Huo, L.; Zhang, Y.; Chu, L. doi:10.1002/9783527834242.chf0204
  • Han, F.; Choi, P. H.; Ye, C.-X.; Grell, Y.; Xie, X.; Ivlev, S. I.; Chen, S.; Meggers, E. Cyclometalated Chiral-at-Ruthenium Catalyst for Enantioselective Ring-Closing C(sp3)–H Carbene Insertion to Access Chiral Flavanones. ACS Catalysis 2022, 12, 10304–10312. doi:10.1021/acscatal.2c02423
  • Wang, P.; Gong, Y.; Wang, X.; Ren, Y.; Wang, L.; Zhai, L.; Li, H.; She, X. Solvent-free, B(C6 F5 )3 -Catalyzed S-H Insertion of Thiophenols and Thiols with α-Diazoesters. Chemistry, an Asian journal 2022, 17, e202200465. doi:10.1002/asia.202200465
  • Li, N.; Yang, X.; Zhu, Y.; Wang, F.; Gong, J.-F.; Song, M.-P. Pincer iridium(III)-catalyzed enantioselective C(sp3)-H functionalization via carbenoid C-H insertion of 3-diazooxindoles with 1,4-cyclohexadiene. Chinese Chemical Letters 2022, 33, 2437–2441. doi:10.1016/j.cclet.2021.11.067
  • Kim, D.-H.; Kim, H.-M.; Lim, J.-S.; Lee, H.-W.; Cho, C.-G. Asymmetric Divergent Total Syntheses of (+)-Decursivine and (+)- Serotobenine via Intramolecular Fischer Indole Synthesis. Organic letters 2022, 24, 2873–2877. doi:10.1021/acs.orglett.2c00848
  • Athavale, S. V.; Chen, K.; Arnold, F. H. doi:10.1002/9783527829170.ch4
  • Dasgupta, A.; Richards, E.; Melen, R. L. Triarylborane Catalyzed Carbene Transfer Reactions Using Diazo Precursors. ACS catalysis 2021, 12, 442–452. doi:10.1021/acscatal.1c04746
  • Pal, K.; Volla, C. M. R. Catalytic Insertion Reactions of α-Imino Carbenoids. Chemical record (New York, N.Y.) 2021, 21, 4032–4058. doi:10.1002/tcr.202100238
  • Sambiagio, C.; Maes, B. U. W. Remote CH Bond Functionalizations; Wiley, 2021; pp 343–382. doi:10.1002/9783527824137.ch12
  • Babu, S. A.; Padmavathi, R.; Suwasia, S.; Dalal, A.; Bhattacharya, D.; Singh, P.; Tomar, R. Recent developments on the synthesis of functionalized carbohydrate/sugar derivatives involving the transition metal–catalyzed C–H activation/C–H functionalization. Studies in Natural Products Chemistry; Elsevier, 2021; Vol. 71, pp 311–399. doi:10.1016/b978-0-323-91095-8.00001-5
  • Woźniak, Ł.; Tan, J.-F.; Nguyen, Q.-H.; du Vigné, A. M.; Smal, V.; Cao, Y.-X.; Cramer, N. Catalytic Enantioselective Functionalizations of C-H Bonds by Chiral Iridium Complexes. Chemical reviews 2020, 120, 10516–10543. doi:10.1021/acs.chemrev.0c00559
Other Beilstein-Institut Open Science Activities