Abstract
Iron-catalyzed C–H amination reactions have emerged as a potent tool in synthetic organic chemistry in recent years. These reactions are eco-friendly, highly catalytic efficient, and show good functional group tolerance. The organonitrogen products of the reaction have found wide applications in agricultural chemistry, medicinal chemistry, industrial chemistry, and natural product synthesis. This review focuses on the recent progress in iron-catalyzed C–H amination reactions and covers literature from 2019-2021.
Keywords: Iron catalysis, oxidative amination, reductive amination, C-N bond, green chemistry, natural product synthesis.
Graphical Abstract
[http://dx.doi.org/10.1021/ar0000354] [PMID: 11456474]
[http://dx.doi.org/10.1021/cr020045d] [PMID: 12744700]
[http://dx.doi.org/10.1021/acssuschemeng.7b03373]
[http://dx.doi.org/10.1002/aoc.5611]
[http://dx.doi.org/10.1055/s-0040-1707128]
[http://dx.doi.org/10.1002/ijch.201900143]
[http://dx.doi.org/10.1039/c1cs15100b] [PMID: 21731959]
[http://dx.doi.org/10.1038/nchem.2388] [PMID: 26673267]
[http://dx.doi.org/10.1002/chem.201403956] [PMID: 25220941]
[http://dx.doi.org/10.1002/anie.201710330] [PMID: 29228463]
[http://dx.doi.org/10.1002/chem.201201329] [PMID: 22736530]
[http://dx.doi.org/10.1021/acs.joc.5b00868] [PMID: 26024300]
[http://dx.doi.org/10.1039/C8CC05979A] [PMID: 30141796]
[http://dx.doi.org/10.1021/ja057222n] [PMID: 16390133]
[http://dx.doi.org/10.1021/cr00098a014]
[http://dx.doi.org/10.1039/C9GC03655E]
[http://dx.doi.org/10.1002/1521-3773(20011105)40:21<3983:AID-ANIE3983>3.0.CO;2-8] [PMID: 12404468]
[http://dx.doi.org/10.1021/ja2092954] [PMID: 21995503]
[http://dx.doi.org/10.1021/ja9046075] [PMID: 19761183]
[http://dx.doi.org/10.1021/om900275j]
[http://dx.doi.org/10.1002/anie.200800497] [PMID: 18663711]
[http://dx.doi.org/10.1002/anie.201201945] [PMID: 22730346]
[http://dx.doi.org/10.1039/C7QO00547D]
[http://dx.doi.org/10.1021/ar200318q] [PMID: 22546004]
[http://dx.doi.org/10.1038/nature06485] [PMID: 18216847]
[http://dx.doi.org/10.1002/anie.201201666] [PMID: 22887739]
[http://dx.doi.org/10.1016/j.tet.2021.132474]
[http://dx.doi.org/10.1039/D0CY02087G]
[http://dx.doi.org/10.1038/nchem.2366] [PMID: 26587714]
[http://dx.doi.org/10.1038/s41557-018-0020-0] [PMID: 29713037]
[http://dx.doi.org/10.1021/ol000107r] [PMID: 10930251]
[http://dx.doi.org/10.1021/jacs.7b05253] [PMID: 28628321]
[http://dx.doi.org/10.1038/ncomms6602] [PMID: 25424885]
[http://dx.doi.org/10.1007/s11434-012-5151-x]
[http://dx.doi.org/10.1351/PAC-CON-11-11-08]
[http://dx.doi.org/10.1038/nature14127] [PMID: 25631448]
[http://dx.doi.org/10.1021/acscentsci.6b00214] [PMID: 27800554]
[http://dx.doi.org/10.1039/b710677g] [PMID: 17989819]
[http://dx.doi.org/10.1021/jacs.9b06035] [PMID: 31274311]
[http://dx.doi.org/10.1039/C5SC01162K] [PMID: 29435216]
[http://dx.doi.org/10.1002/anie.201710931] [PMID: 29160920]
[http://dx.doi.org/10.1021/jacs.8b11466] [PMID: 30558415]
[http://dx.doi.org/10.1021/ol301847m] [PMID: 22849697]
[http://dx.doi.org/10.1021/cs501045v] [PMID: 25243095]
[http://dx.doi.org/10.1039/C7CC08181B] [PMID: 29250630]
[http://dx.doi.org/10.1021/acscatal.6b00865]
[http://dx.doi.org/10.1021/acscatal.0c00393]
[http://dx.doi.org/10.1021/ol0273396] [PMID: 12633073]
[http://dx.doi.org/10.1039/B918588G] [PMID: 20107651]
[http://dx.doi.org/10.1021/om300840z]
[http://dx.doi.org/10.1021/cr500410y] [PMID: 25531056]
[http://dx.doi.org/10.1002/slct.201904436]
[http://dx.doi.org/10.1021/ja202563w] [PMID: 21520961]
[http://dx.doi.org/10.1039/c3cc44435j] [PMID: 23945918]
[http://dx.doi.org/10.1039/C9GC02625H]
[http://dx.doi.org/10.1039/C7NJ02727C]
[http://dx.doi.org/10.1002/anie.201806434] [PMID: 30016576]
[http://dx.doi.org/10.1039/c0cc05811d] [PMID: 21327194]
[http://dx.doi.org/10.1021/acscatal.0c04608] [PMID: 34336370]
[http://dx.doi.org/10.1021/acs.joc.1c01602] [PMID: 34387487]
[http://dx.doi.org/10.1021/acs.joc.0c02843] [PMID: 33443426]
[http://dx.doi.org/10.1021/acs.organomet.1c00032]
[http://dx.doi.org/10.1039/c39890000116]
[http://dx.doi.org/10.1039/c2cc34634f] [PMID: 22992783]
[http://dx.doi.org/10.1039/B412016G] [PMID: 15543274]
[http://dx.doi.org/10.1016/1352-2310(94)90405-7]
[http://dx.doi.org/10.1002/anie.202014950] [PMID: 33463874]
[http://dx.doi.org/10.1039/C7CC02801F] [PMID: 28574557]
[http://dx.doi.org/10.1039/D0CC04579A] [PMID: 33000809]
[http://dx.doi.org/10.1039/c3ra46363j]
[http://dx.doi.org/10.1021/acs.orglett.0c02671] [PMID: 32870016]
[http://dx.doi.org/10.1016/j.jorganchem.2021.122174]
[http://dx.doi.org/10.1021/acs.joc.6b01827] [PMID: 27736056]
[http://dx.doi.org/10.1021/ja402479r] [PMID: 23734676]
[http://dx.doi.org/10.1002/adsc.201100334]
[http://dx.doi.org/10.1039/c4ra04037f]
[http://dx.doi.org/10.1021/acscatal.1c02432]
[http://dx.doi.org/10.1039/D1RA00012H]
[http://dx.doi.org/10.1039/C2CY00376G]
[http://dx.doi.org/10.1007/978-1-4684-3240-4_2]
[http://dx.doi.org/10.1021/acs.chemrev.6b00644] [PMID: 28051855]
[http://dx.doi.org/10.1016/j.tet.2019.130607]
[http://dx.doi.org/10.1021/jacs.9b13753] [PMID: 32090542]
[http://dx.doi.org/10.1002/ajoc.201900641]
[http://dx.doi.org/10.1002/ejoc.201901614]
[http://dx.doi.org/10.1021/acs.orglett.1c00099] [PMID: 33544600]
[http://dx.doi.org/10.1021/acs.orglett.0c00296] [PMID: 32049535]
[http://dx.doi.org/10.1002/anie.201911704] [PMID: 31599056]
[http://dx.doi.org/10.1021/acs.orglett.0c02574] [PMID: 32903001]
[http://dx.doi.org/10.1039/D0SC00784F] [PMID: 34122922]
[http://dx.doi.org/10.1002/ejoc.201901864]
[http://dx.doi.org/10.1039/D1CY00682G]
[http://dx.doi.org/10.1039/D0OB01241F] [PMID: 32662797]
[http://dx.doi.org/10.1002/anie.202013687] [PMID: 33301240]
[http://dx.doi.org/10.1002/ejoc.202100010]
[http://dx.doi.org/10.1002/cssc.202000856] [PMID: 32314866]
[http://dx.doi.org/10.1002/cjoc.202000299]
[http://dx.doi.org/10.1021/jacs.0c07810] [PMID: 32893615]
[http://dx.doi.org/10.1002/cbic.201900783] [PMID: 32189465]