Journal of the American Chemical Society
Page 10 of 11
Wang, J.; Shi, X.; Li, F. Iodine-catalyzed diazoactivation to
(d) Yuan, Y.-A.; Lu, D.-F.; Chen, Y.-R.; Xu, H. Iron-catalyzed
access radical reactivity. Nat. Commun. 2018, 9, 1972. (f)
Grotenhuis, C.; Heuvel, N.; Vlugt, J. I.; Bruin, B. Catalytic
dibenzocyclooctene synthesis via cobalt(III)–carbene
radical and orthoquinodimethane intermediates. Angew.
Chem. Int. Ed. 2018, 57, 140-145. (g) Ciszewski, Ł. W.;
Rybicka-Jasińska, K.; Gryko, D. Recent developments in
photochemical reactions of diazo compounds. Org. Biomol.
Chem. 2019, 17, 432-448.
direct diazidation for a broad range of olefins. Angew. Chem.
Int. Ed. 2016, 55, 534-538. (e) Fu, N.; Sauer, G. S.; Saha, A.;
Loo, A.; Lin. S. Metal-catalyzed electrochemical diazidation
of alkenes. Science 2017, 357, 575-579.
1
2
3
4
5
6
(12) Ratnikov, M. O.; Farkas, L. E.; Doyle, M. P. Tandem sequence
of phenol oxidation and intramolecular addition as a
method in building heterocycles. J. Org. Chem. 2012, 77,
10294-10303.
7
8
9
(6) (a) Cukier, R. I.; Nocera, D. G. Proton-coupled electron
transfer. Annu. Rev. Phys. Chem. 1998, 49, 337-369. (b)
Hatcher, E.; Soudackov, A. V.; Hammes-Schiffer, S. Proton-
coupled electron transfer in soybean lipoxygenase. J. Am.
Chem. 2004, 126, 5763-5775. (c) Huynh, M. H. V.; Meyer, T.
J. Proton-coupled electron transfer. Chem. Rev. 2007, 107,
5004−5064. (d) Gentry, E. C.; Knowles, R. R. Synthetic
applications of proton-coupled electron transfer. Acc.
Chem. Res. 2016, 49, 1546-1556. (e) Mora, S. J.; Odella, E.;
Moore, G. F.; Gust, D.; Moore, T. A.; Moore, A. L. Proton-
Coupled Electron Transfer in Artificial Photosynthetic
Systems. Acc. Chem. Res. 2018, 51, 445-453.
(7) (a) Simón, L.; Goodman, J. M. Theoretical study of the
mechanism of Hantzsch ester hydrogenation of imines
catalyzed by chiral BINOL-phosphoric acids. J. Am. Chem.
2008, 130, 8741-8747. (b) Chen, Q.-A.; Chen, M.-W.; Yu, C.-
B.; Shi, L.; Wang, D.-S.; Yang, Y.; Zhou, Y.-G. Biomimetic
asymmetric hydrogenation: in situ regenerable Hantzsch
esters for asymmetric hydrogenation of benzoxazinones. J.
Am. Chem. 2011, 133, 16432-16435. (c) Zheng, C.; You, S.-
L. Transfer hydrogenation with Hantzsch esters and
related organic hydride donors. Chem. Soc. Rev. 2012, 41,
2498-2518. (d) Qi, L.; Chen, Y. Polarity-reversed allylations
of aldehydes, ketones, and imines enabled by Hantzsch
ester in photoredox catalysis. Angew. Chem. Int. Ed. 2016,
55, 13312-13315. (e) Huang, W.; Cheng, X. Hantzsch esters
as multifunctional reagents in visible-light photoredox
catalysis. Synlett 2017, 28, 148-158. (f) Wang, P. Z.; Chen, J.
R.; Xiao, W. J. Hantzsch esters: an emerging versatile class
of reagents in photoredox catalyzed organic synthesis. Org.
Biomol. Chem. 2019, 17, 6936-6951.
(8) (a) Prier, C. K.; Rankic, D. A.; Macmillan, D. W. C. Visible light
photoredox catalysis with transition metal complexes:
applications in organic synthesis. Chem. Rev. 2013, 113,
5322-5363. (b) Schultz, D. M.; Yoon, T. P. Solar synthesis:
prospects in visible light photocatalysis. Science 2014, 343,
1239176. (c) Twilton, J.; Zhang, P.; Shaw, M. H.; Evans, R.
W.; MacMillan, D. W. The merger of transition metal and
photocatalysis. Nat. Rev. Chem. 2017, 1, 1-19.
(9) Seath, C. P.; Vogt, D. B.; Xu, Z.; Boyington, A. J.; Jui, N. T.
Radical hydroarylation of functionalized olefins and
mechanistic investigation of photocatalytic pyridyl radical
reactions. J. Am. Chem. Soc. 2018, 140, 15525-15534.
(10) (a) Hili, R.; Yudin, A. K. Making carbon-nitrogen bonds in
biological and chemical synthesis. Nat. Chem. Biol. 2006, 2,
284-287. (b) Bariwal, J.; Van der Eycken, E. C-N bond
forming cross-coupling reactions: an overview. Chem. Soc.
Rev. 2013, 42, 9283-9283. (c) Ruiz-Castillo, P.; Buchwald, S.
L. Application of palladium-catalyzed C–N cross-coupling
reactions. Chem. Rev. 2016, 116, 12564-12649. (d) Liu, Y.;
You, T.; Wang, T.-T.; Che, C.-M. Iron-catalyzed C–H
amination and its application in organic synthesis.
Tetrahedron 2019, 75, 130607-130625.
(13) Neff, R. K.; Su, Y.-L.; Liu, S.; Rosado, M.; Zhang, X.; Doyle, M.
P. Generation of halomethyl radicals by halogen atom
abstraction and their addition reactions with alkenes. J. Am.
Chem. Soc. 2019, 141, 16643-16650.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(14) (a) Zard, S. Z. Recent progress in the generation and use of
nitrogen-centered radicals. Chem. Soc. Rev. 2008, 37, 1603-
1618. (b) Sun, X.; Yu, S. Visible-light-promoted iminyl
radical formation from vinyl azides: synthesis of 6-
(fluoro)alkylated phenanthridines. Chem. Commun. 2016,
52, 10898-10901. (c) Fu, J.; Zanoni, G.; Anderson, E. A.; Bi,
X. α-Substituted vinyl azides: an emerging functionalized
alkene. Chem. Soc. Rev. 2017, 46, 7208-7228. (d) Ning, Y.;
Zhao, X.-F.; Wu, Y.-B.; Bi, X., Radical Enamination of Vinyl
Azides: Direct synthesis of N-unprotected enamines. Org.
Lett. 2017, 19, 6240-6243.
(15) (a) Ciszewski, Ł. W.; Durka, J.; Gryko, D. Photocatalytic
alkylation of pyrroles and indoles with α‑diazo esters. Org.
Lett. 2019, 21, 7028-7032. (b) Zheng, C.; Wang, Y.; Xu, Y.;
Chen, Z.; Chen, G.; Liang, S. H. Ru-photoredox-catalyzed
decarboxylative oxygenation of aliphatic carboxylic acids
through N‑(acyloxy)phthalimide. Org. Lett. 2018, 20, 482 4-
4827.
(16) (a) Sumino, S.; Fusano, A.; Ryu, I. Reductive bromine atom-
transfer reaction. Org. Lett. 2013, 15, 2826-2829. (b)
Trowbridge, A.; Reich, D.; Gaunt, M. J. Multicomponent
synthesis of tertiary alkylamines by photocatalytic olefin-
hydroaminoalkylation. Nature 2018, 561, 522-527. (c)
Zhang, L. M.; Si, X. J.; Yang, Y. Y.; Witzel, S.; Sekine, K.;
Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Reductive C-C
coupling by desulfurizing gold-catalyzed photoreactions.
ACS Catal. 2019, 9, 6118-6123. (d) Wu, J. J.; Grant, P. S.; Li,
X. B.; Noble, A.; Aggarwal, V. K. Catalyst-free deaminative
functionalizations of primary amines by photoinduced
single-electron transfer. Angew. Chem. Int. Ed. 2019, 58,
5697-5701. (e) Li, Z.-L.; Fang, G.-C.; Gu, Q.-S.; Liu, X.-Y.
Recent advances in copper-catalysed radical-involved
asymmetric 1,2-difunctionalization of alkenes. Chem. Soc.
Rev. 2020, 49, 32-48. (f) Schwarz, J. L.; Huang, H.-M.;
Paulisch, T. O.; Glorius, F. Dialkylation of 1,3-dienes by dual
photoredox and chromium catalysis. ACS Catal. 2020, 10,
1621-1627.
(17) (a) Huang, W.; Chen, W.; Wang, G.; Li, J.; Cheng, X.; Li, G.
Thiyl-radical-catalyzed
photoreductive
hydrodifluoroacetamidation of alkenes with Hantzsch
ester as a multifunctional reagent. ACS Catal. 2016, 6, 7471-
7474. (b) Huang, W. H.; Chen, J. Z.; Hong, D. C.; Chen, W. X.;
Cheng,
X.;
Tian,
Y.
X.;
Li,
G.
G.
Hydrophosphonodifluoromethylation of alkenes via thiyl-
radical/photoredox catalysis. J. Org. Chem. 2018, 83, 578-
587.
(18) (a) Ratnikov, M. O.; Doyle, M. P. Mechanistic investigation
of oxidative Mannich reaction with tert-butyl
hydroperoxide. The role of transition metal salt. J. Am.
Chem. Soc. 2013, 135, 1549-1557. (b) Barton, D. H. R.; Le
Gloahec, V. N.; Patin, H.; Launay, F. Radical chemistry of
tert-butyl hydroperoxide (TBHP). Part 1. Studies of the
FeIII-TBHP mechanism. New J. Chem. 1998, 22, 559-563.
(19) (a) Zhu, X.; Chiba, S. Copper-catalyzed oxidative carbon–
heteroatom bond formation: a recent update. Chem. Soc.
Rev. 2016, 45, 4504-4523. (b) Flodén, N. J.; Trowbridge, A.;
(11) (a) Waser, J.; Nambu, H.; Carreira, E. M. Cobalt-catalyzed
hydroazidation of olefins: convenient access to alkyl azides.
J. Am. Chem. Soc. 2005, 127, 8294-8295. (b) Sharma, A.;
Hartwig, J. F. Metal-catalysed azidation of tertiary C-H
bonds suitable for late-stage functionalization. Nat ure
2015, 517, 600-604. (c) Organic Azides: Syntheses and
Applications; Bräse, S. & Banert, K. Wiley: New York, 2010.
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