-
1
-
-
85043097618
-
-
For selected reviews on catalytic cross-coupling reactions of unactivated alkyl halides through nucleophile/electrophile regimes, see
-
For selected reviews on catalytic cross-coupling reactions of unactivated alkyl halides through nucleophile/electrophile regimes, see:
-
-
-
-
2
-
-
81355154663
-
-
X. Hu, Chem. Sci. 2011, 2, 1867–1886;
-
(2011)
Chem. Sci.
, vol.2
, pp. 1867-1886
-
-
Hu, X.1
-
3
-
-
79952656192
-
-
R. Jana, T. P. Pathak, M. S. Sigman, Chem. Rev. 2011, 111, 1417–1492;
-
(2011)
Chem. Rev.
, vol.111
, pp. 1417-1492
-
-
Jana, R.1
Pathak, T.P.2
Sigman, M.S.3
-
5
-
-
21244446092
-
-
Angew. Chem. 2005, 117, 680–695;
-
(2005)
Angew. Chem.
, vol.117
, pp. 680-695
-
-
-
8
-
-
3042657024
-
-
Angew. Chem. 2003, 115, 398–401.
-
(2003)
Angew. Chem.
, vol.115
, pp. 398-401
-
-
-
9
-
-
85043101041
-
-
For reviews on cross-electrophile couplings of organic halides, see
-
For reviews on cross-electrophile couplings of organic halides, see:
-
-
-
-
10
-
-
84941780112
-
-
J. Gu, X. Wang, W. Xue, H. Gong, Org. Chem. Front. 2015, 2, 1411–1421;
-
(2015)
Org. Chem. Front.
, vol.2
, pp. 1411-1421
-
-
Gu, J.1
Wang, X.2
Xue, W.3
Gong, H.4
-
12
-
-
84903272376
-
-
T. Moragas, A. Correa, R. Martin, Chem. Eur. J. 2014, 20, 8242–8258;
-
(2014)
Chem. Eur. J.
, vol.20
, pp. 8242-8258
-
-
Moragas, T.1
Correa, A.2
Martin, R.3
-
13
-
-
84901349795
-
-
C. E. I. Knappke, S. Grupe, D. Gärtner, M. Corpet, C. Gosmini, A. Jacobi von Wangelin, Chem. Eur. J. 2014, 20, 6828–6842.
-
(2014)
Chem. Eur. J.
, vol.20
, pp. 6828-6842
-
-
Knappke, C.E.I.1
Grupe, S.2
Gärtner, D.3
Corpet, M.4
Gosmini, C.5
Jacobi von Wangelin, A.6
-
14
-
-
33947090537
-
-
S. Ozaki, Chem. Rev. 1972, 72, 457–496;
-
(1972)
Chem. Rev.
, vol.72
, pp. 457-496
-
-
Ozaki, S.1
-
16
-
-
85099671346
-
-
For seminal stoichiometric studies of Ni, complexes with isocyanates, see
-
0 complexes with isocyanates, see:
-
-
-
-
18
-
-
33947136143
-
-
H. Hoberg, K. Summermann, A. Milchereit, J. Organomet. Chem. 1985, 288, 237–248;
-
(1985)
J. Organomet. Chem.
, vol.288
, pp. 237-248
-
-
Hoberg, H.1
Summermann, K.2
Milchereit, A.3
-
20
-
-
84990199531
-
-
Angew. Chem. 1985, 97, 987–988;
-
(1985)
Angew. Chem.
, vol.97
, pp. 987-988
-
-
-
22
-
-
85043118375
-
-
For selected Ni-catalyzed reactions of isocyanates with coupling partners other than organic halides, see
-
For selected Ni-catalyzed reactions of isocyanates with coupling partners other than organic halides, see:
-
-
-
-
23
-
-
78449237761
-
-
T. Miura, M. Morimoto, M. Murakami, J. Am. Chem. Soc. 2010, 132, 15836–15838;
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 15836-15838
-
-
Miura, T.1
Morimoto, M.2
Murakami, M.3
-
24
-
-
77958467791
-
-
T. Ozawa, H. Horie, T. Kurahashi, S. Matsubara, Chem. Commun. 2010, 46, 8055–8057;
-
(2010)
Chem. Commun.
, vol.46
, pp. 8055-8057
-
-
Ozawa, T.1
Horie, H.2
Kurahashi, T.3
Matsubara, S.4
-
27
-
-
4544240649
-
-
H. A. Duong, M. Cross, J. Louie, J. Am. Chem. Soc. 2004, 126, 11438–11439.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 11438-11439
-
-
Duong, H.A.1
Cross, M.2
Louie, J.3
-
31
-
-
0003463819
-
-
(Eds., Wiley-Interscience, New Yor
-
The Amide Linkage: Structural Significance in Chemistry, Biochemistry and Materials Science (Eds.: A. Greenberg, C. M. Breneman, J. F. Liebman), Wiley-Interscience, New York, 2000;
-
(2000)
The Amide Linkage: Structural Significance in Chemistry, Biochemistry and Materials Science
-
-
Greenberg, A.1
Breneman, C.M.2
Liebman, J.F.3
-
32
-
-
33745079610
-
-
J. S. Carey, D. Laffan, C. Thomson, M. T. Williams, Org. Biomol. Chem. 2006, 4, 2337–2347.
-
(2006)
Org. Biomol. Chem.
, vol.4
, pp. 2337-2347
-
-
Carey, J.S.1
Laffan, D.2
Thomson, C.3
Williams, M.T.4
-
33
-
-
85043116297
-
-
For selected elegant reviews on amide bond formation, se
-
For selected elegant reviews on amide bond formation, see:
-
-
-
-
38
-
-
85043121580
-
-
For selected examples, se
-
For selected examples, see:
-
-
-
-
39
-
-
84935925769
-
-
G. Zhang, B. Gao, H. Huang, Angew. Chem. Int. Ed. 2015, 54, 7657–7661;
-
(2015)
Angew. Chem. Int. Ed.
, vol.54
, pp. 7657-7661
-
-
Zhang, G.1
Gao, B.2
Huang, H.3
-
40
-
-
84939653128
-
-
Angew. Chem. 2015, 127, 7767–7771;
-
(2015)
Angew. Chem.
, vol.127
, pp. 7767-7771
-
-
-
41
-
-
84929376729
-
-
K. Dong, X. Fang, R. Jackstell, G. Laurenczy, Y. Li, M. Beller, J. Am. Chem. Soc. 2015, 137, 6053–6058;
-
(2015)
J. Am. Chem. Soc.
, vol.137
, pp. 6053-6058
-
-
Dong, K.1
Fang, X.2
Jackstell, R.3
Laurenczy, G.4
Li, Y.5
Beller, M.6
-
42
-
-
84904109476
-
-
C. Jiménez-Rodriguez, A. A. Núñez-Magro, T. Seidensticker, G. R. Eastham, M. R. L. Furst, D. J. Cole-Hamilton, Catal. Sci. Technol. 2014, 4, 2332–2339;
-
(2014)
Catal. Sci. Technol.
, vol.4
, pp. 2332-2339
-
-
Jiménez-Rodriguez, C.1
Núñez-Magro, A.A.2
Seidensticker, T.3
Eastham, G.R.4
Furst, M.R.L.5
Cole-Hamilton, D.J.6
-
43
-
-
84903201085
-
-
H. Liu, N. Yan, P. J. Dyson, Chem. Commun. 2014, 50, 7848–7851;
-
(2014)
Chem. Commun.
, vol.50
, pp. 7848-7851
-
-
Liu, H.1
Yan, N.2
Dyson, P.J.3
-
44
-
-
84890664637
-
-
X. Fang, R. Jackstell, M. Beller, Angew. Chem. Int. Ed. 2013, 52, 14089–14093;
-
(2013)
Angew. Chem. Int. Ed.
, vol.52
, pp. 14089-14093
-
-
Fang, X.1
Jackstell, R.2
Beller, M.3
-
45
-
-
84922657221
-
-
Angew. Chem. 2013, 125, 14339–14343;
-
(2013)
Angew. Chem.
, vol.125
, pp. 14339-14343
-
-
-
46
-
-
33845681216
-
-
T. Fukuyama, T. Inouye, I. Ryu, J. Organomet. Chem. 2007, 692, 685–690;
-
(2007)
J. Organomet. Chem.
, vol.692
, pp. 685-690
-
-
Fukuyama, T.1
Inouye, T.2
Ryu, I.3
-
47
-
-
0002629226
-
-
references therein
-
I. Ryu, K. Nagahara, N. Kambe, N. Sonoda, S. Kreimerman, M. Komatsu, Chem. Commun. 1998, 1953–1954, and references therein.
-
(1998)
Chem. Commun.
, pp. 1953-1954
-
-
Ryu, I.1
Nagahara, K.2
Kambe, N.3
Sonoda, N.4
Kreimerman, S.5
Komatsu, M.6
-
48
-
-
85043130645
-
-
Selected examples on using organometallic reagents with β-hydrogen atoms. For RMgX, se
-
Selected examples on using organometallic reagents with β-hydrogen atoms. For RMgX, see:
-
-
-
-
49
-
-
84865844652
-
-
G. Schäfer, C. Matthey, J. W. Bode, Angew. Chem. Int. Ed. 2012, 51, 9173–9175;
-
(2012)
Angew. Chem. Int. Ed.
, vol.51
, pp. 9173-9175
-
-
Schäfer, G.1
Matthey, C.2
Bode, J.W.3
-
50
-
-
84920711227
-
-
For RLi, se
-
Angew. Chem. 2012, 124, 9307–9310. For RLi, see:
-
(2012)
Angew. Chem.
, vol.124
, pp. 9307-9310
-
-
-
51
-
-
84883249682
-
-
V. Pace, L. Castoldi, W. Holzer, Chem. Commun. 2013, 49, 8383–8385, and
-
(2013)
Chem. Commun.
, vol.49
, pp. 8383-8385
-
-
Pace, V.1
Castoldi, L.2
Holzer, W.3
-
52
-
-
33747761620
-
-
references therein
-
I. Coldham, S. Dufour, T. F. N. Haxell, J. J. Patel, G. Sanchez-Jimenez, J. Am. Chem. Soc. 2006, 128, 10943–10951, and references therein.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 10943-10951
-
-
Coldham, I.1
Dufour, S.2
Haxell, T.F.N.3
Patel, J.J.4
Sanchez-Jimenez, G.5
-
53
-
-
85043141751
-
-
Recently, intermolecular catalytic hydrocarbamoylation reactions of noncyclic alkenes with formamides have been reported for forging aliphatic amide bonds possessing β-hydrogens. In all cases α-branched amides could not be achieved, obtaining exclusive linear selectivity. For examples, see
-
Recently, intermolecular catalytic hydrocarbamoylation reactions of noncyclic alkenes with formamides have been reported for forging aliphatic amide bonds possessing β-hydrogens. In all cases α-branched amides could not be achieved, obtaining exclusive linear selectivity. For examples, see:
-
-
-
-
54
-
-
84952342780
-
-
T. Seidensticker, M. R. L. Furst, R. Frauenlob, J. Vondran, E. Paetzold, U. Kragl, A. J. Vorhold, ChemCatChem 2015, 7, 4085–4090;
-
(2015)
ChemCatChem
, vol.7
, pp. 4085-4090
-
-
Seidensticker, T.1
Furst, M.R.L.2
Frauenlob, R.3
Vondran, J.4
Paetzold, E.5
Kragl, U.6
Vorhold, A.J.7
-
55
-
-
84859516883
-
-
Y. Miyazaki, Y. Yamada, Y. Nakao, T. Hiyama, Chem. Lett. 2012, 41, 298–300;
-
(2012)
Chem. Lett.
, vol.41
, pp. 298-300
-
-
Miyazaki, Y.1
Yamada, Y.2
Nakao, Y.3
Hiyama, T.4
-
56
-
-
0141520397
-
-
S. Ko, H. Han, S. Chang, Org. Lett. 2003, 5, 2687–2690.
-
(2003)
Org. Lett.
, vol.5
, pp. 2687-2690
-
-
Ko, S.1
Han, H.2
Chang, S.3
-
57
-
-
85043102702
-
-
For selected recent examples, se
-
For selected recent examples, see:
-
-
-
-
58
-
-
84906092265
-
-
Y. Liu, J. Cornella, R. Martin, J. Am. Chem. Soc. 2014, 136, 11212–11215;
-
(2014)
J. Am. Chem. Soc.
, vol.136
, pp. 11212-11215
-
-
Liu, Y.1
Cornella, J.2
Martin, R.3
-
59
-
-
84919941481
-
-
T. Moragas, J. Cornella, R. Martin, J. Am. Chem. Soc. 2014, 136, 17702–17705;
-
(2014)
J. Am. Chem. Soc.
, vol.136
, pp. 17702-17705
-
-
Moragas, T.1
Cornella, J.2
Martin, R.3
-
60
-
-
84930216584
-
-
X. Wang, Y. Liu, R. Martin, J. Am. Chem. Soc. 2015, 137, 6476–6479;
-
(2015)
J. Am. Chem. Soc.
, vol.137
, pp. 6476-6479
-
-
Wang, X.1
Liu, Y.2
Martin, R.3
-
61
-
-
84937685163
-
-
X. Wang, M. Nakajima, R. Martin, J. Am. Chem. Soc. 2015, 137, 8924–8927.
-
(2015)
J. Am. Chem. Soc.
, vol.137
, pp. 8924-8927
-
-
Wang, X.1
Nakajima, M.2
Martin, R.3
-
62
-
-
84906291881
-
-
in, (Eds., A. R. Katritzky, R. J. K. Taylor, Elsevier, Oxfor
-
P. D. Bailey, T. J. Mills, R. Pettecrew, R. A. Price, in Comprehensive Organic Functional Groups Transformation II, Vol. 5 (Eds.: A. R. Katritzky, R. J. K. Taylor), Elsevier, Oxford, 2005, pp. 201–294.
-
(2005)
Comprehensive Organic Functional Groups Transformation II, Vol. 5
, pp. 201-294
-
-
Bailey, P.D.1
Mills, T.J.2
Pettecrew, R.3
Price, R.A.4
-
63
-
-
85043126767
-
-
See the Supporting information for details
-
See the Supporting information for details.
-
-
-
-
64
-
-
84982077610
-
-
L2 can be prepared in two steps and on a multigram scale following a slightly modified literature procedur
-
L2 can be prepared in two steps and on a multigram scale following a slightly modified literature procedure: T. Kauffmann, J. König, A. Woltermann, Chem. Ber. 1976, 109, 3864–3868.
-
(1976)
Chem. Ber.
, vol.109
, pp. 3864-3868
-
-
Kauffmann, T.1
König, J.2
Woltermann, A.3
-
65
-
-
85043138419
-
-
For the early use of bipyridine and phenanthroline ligands in cross-coupling reactions of unactivated alkyl halides, se
-
For the early use of bipyridine and phenanthroline ligands in cross-coupling reactions of unactivated alkyl halides, see:
-
-
-
-
67
-
-
12944309312
-
-
D. A. Powell, T. Maki, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 510–511.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 510-511
-
-
Powell, D.A.1
Maki, T.2
Fu, G.C.3
-
68
-
-
84990173995
-
-
Whereas L1 and L5 predominantly lead to homodimerization, significant amounts of β-hydride elimination and reduction products were observed when usin
-
Whereas L1 and L5 predominantly lead to homodimerization, significant amounts of β-hydride elimination and reduction products were observed when using L4.
-
-
-
-
69
-
-
85043133207
-
-
Note, however, that L3 turned out to be particularly efficient for aryl isocianates (see Scheme 3
-
Note, however, that L3 turned out to be particularly efficient for aryl isocianates (see Scheme 3).
-
-
-
-
70
-
-
85043125267
-
-
Full conversion to β-hydride elimination products was observed for 1 a-I. The observed reactivity of 1 a-OTs is in line with the ability of these substrates to couple with other heterocumulenes (see Ref. [13 a]
-
Full conversion to β-hydride elimination products was observed for 1 a-I. The observed reactivity of 1 a-OTs is in line with the ability of these substrates to couple with other heterocumulenes (see Ref. [13 a]).
-
-
-
-
71
-
-
85043098035
-
-
Unlike the utilization of aliphatic isocyanates, equimolar amounts of aromatic isocyanates were critical to prevent the formation of considerable amounts of N-acylureas
-
Unlike the utilization of aliphatic isocyanates, equimolar amounts of aromatic isocyanates were critical to prevent the formation of considerable amounts of N-acylureas.
-
-
-
-
72
-
-
85043127268
-
-
turned out to be particularly suited for the coupling of iPrNCO, avoiding dimerization or trimerization pathways
-
[(TMEDA)Ni(o-tolyl)Cl] turned out to be particularly suited for the coupling of iPrNCO, avoiding dimerization or trimerization pathways.
-
-
-
-
73
-
-
85043106093
-
-
This hypothesis is reinforced by the significant inhibition observed when reacting 1 a with 2 a in the presence of radical scavengers such as TEMPO or BHT. The intermediacy of radical-type intermediates gains credence from the observation that the Ni-catalyzed reductive amidation of 6-bromohex-1-ene results in a linear relationship between acyclic and 5-exo-trig cyclization products at different Ni/L2 loading
-
This hypothesis is reinforced by the significant inhibition observed when reacting 1 a with 2 a in the presence of radical scavengers such as TEMPO or BHT. The intermediacy of radical-type intermediates gains credence from the observation that the Ni-catalyzed reductive amidation of 6-bromohex-1-ene results in a linear relationship between acyclic and 5-exo-trig cyclization products at different Ni/L2 loadings.
-
-
-
-
74
-
-
85043136539
-
-
For remarkable exceptions, se
-
For remarkable exceptions, see:
-
-
-
-
75
-
-
84941795343
-
-
X. Wang, S. Wang, W. Xue, H. Gong, J. Am. Chem. Soc. 2015, 137, 11562–11565;
-
(2015)
J. Am. Chem. Soc.
, vol.137
, pp. 11562-11565
-
-
Wang, X.1
Wang, S.2
Xue, W.3
Gong, H.4
-
76
-
-
84919393313
-
-
C. Zhao, X. Jia, X. Wang, H. Gong, J. Am. Chem. Soc. 2014, 136, 17645–17651.
-
(2014)
J. Am. Chem. Soc.
, vol.136
, pp. 17645-17651
-
-
Zhao, C.1
Jia, X.2
Wang, X.3
Gong, H.4
-
77
-
-
85043121445
-
-
Noncaged tertiary alkyl bromides provided traces of products
-
Noncaged tertiary alkyl bromides provided traces of products.
-
-
-
-
78
-
-
33645888707
-
-
A. K. Mahalingam, X. Wu, M. Alterman, Tetrahedron Lett. 2006, 47, 3051–3053.
-
(2006)
Tetrahedron Lett.
, vol.47
, pp. 3051-3053
-
-
Mahalingam, A.K.1
Wu, X.2
Alterman, M.3
-
80
-
-
85099671466
-
-
The isolation of Ni, (L2), proved to be particularly difficult. Stoichiometric studies were performed with Ni, (L3) and NiBr, (L3), as L3 proved superior for aromatic isocyanates
-
2(L3), as L3 proved superior for aromatic isocyanates.
-
-
-
-
81
-
-
85043117211
-
-
CCDC 1481428 (7) and CCDC 1481429 (8) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centr
-
CCDC 1481428 (7) and CCDC 1481429 (8) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
-
-
-
-
82
-
-
85043135460
-
-
β-hydride elimination, reduction, homodimerizationthe formation of N-acylureas account for the mass balance
-
β-hydride elimination, reduction, homodimerization, and the formation of N-acylureas account for the mass balance.
-
-
-
-
83
-
-
85099671572
-
-
At present, we cannot rule out a significant contribution dealing with Ni, intermediates generated via single-electron transfer reduction mediated by Mn, se
-
I intermediates generated via single-electron transfer reduction mediated by Mn, see:
-
-
-
-
84
-
-
17444373959
-
-
E. Duñach, A. P. Esteves, M. J. Medeiros, S. Olivero, New J. Chem. 2005, 29, 633–636;
-
(2005)
New J. Chem.
, vol.29
, pp. 633-636
-
-
Duñach, E.1
Esteves, A.P.2
Medeiros, M.J.3
Olivero, S.4
-
85
-
-
84924282669
-
-
T. Fujihara, Y. Horimoto, T. Mizoe, F. B. Sayyed, Y. Tani, J. Terao, S. Sakaki, Y. Tsuji, Org. Lett. 2014, 16, 4960–4963;
-
(2014)
Org. Lett.
, vol.16
, pp. 4960-4963
-
-
Fujihara, T.1
Horimoto, Y.2
Mizoe, T.3
Sayyed, F.B.4
Tani, Y.5
Terao, J.6
Sakaki, S.7
Tsuji, Y.8
-
86
-
-
23044487249
-
-
M. L. Nadal, J. Bosch, J. M. Vila, G. Klein, S. Ricart, J. M. Moretó, J. Am. Chem. Soc. 2005, 127, 10476–10477.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 10476-10477
-
-
Nadal, M.L.1
Bosch, J.2
Vila, J.M.3
Klein, G.4
Ricart, S.5
Moretó, J.M.6
-
87
-
-
85099670847
-
-
For selected comproportionation events en route to Ni, species, se
-
I species, see:
-
-
-
-
88
-
-
84873385505
-
-
J. Cornella, E. Gómez-Bengoa, R. Martin, J. Am. Chem. Soc. 2013, 135, 1997–2009;
-
(2013)
J. Am. Chem. Soc.
, vol.135
, pp. 1997-2009
-
-
Cornella, J.1
Gómez-Bengoa, E.2
Martin, R.3
-
89
-
-
77953044889
-
-
A. Velian, S. Lin, A. J. M. Miller, M. W. Day, T. Agapie, J. Am. Chem. Soc. 2010, 132, 6296–6297;
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 6296-6297
-
-
Velian, A.1
Lin, S.2
Miller, A.J.M.3
Day, M.W.4
Agapie, T.5
-
90
-
-
36749022699
-
-
V. B. Phapale, E. Buñuel, M. García-Iglesias, D. J. Cárdenas, Angew. Chem. Int. Ed. 2007, 46, 8790–8795;
-
(2007)
Angew. Chem. Int. Ed.
, vol.46
, pp. 8790-8795
-
-
Phapale, V.B.1
Buñuel, E.2
García-Iglesias, M.3
Cárdenas, D.J.4
-
91
-
-
63449111326
-
-
Angew. Chem. 2007, 119, 8946–8951;
-
(2007)
Angew. Chem.
, vol.119
, pp. 8946-8951
-
-
-
92
-
-
33749519198
-
-
G. D. Jones, J. L. Martin, C. McFarland, O. R. Allen, R. E. Hall, A. D. Haley, R. J. Brandon, T. Konovalova, P. J. Desrochers, P. Pulay, D. A. Vicic, J. Am. Chem. Soc. 2006, 128, 13175–13183.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 13175-13183
-
-
Jones, G.D.1
Martin, J.L.2
McFarland, C.3
Allen, O.R.4
Hall, R.E.5
Haley, A.D.6
Brandon, R.J.7
Konovalova, T.8
Desrochers, P.J.9
Pulay, P.10
Vicic, D.A.11
-
93
-
-
84956713020
-
-
Ni, species have been shown to rapidly react with heterocumulenes other than RNCO, se
-
NiIspecies have been shown to rapidly react with heterocumulenes other than RNCO, see: F. S. Menges, S. M. Craig, N. Tötsch, A. Bloomfield, S. Ghosh, H.-J. Krüger, M. A. Johnson, Angew. Chem. Int. Ed. 2016, 55, 1282–1285;
-
(2016)
Angew. Chem. Int. Ed.
, vol.55
, pp. 1282-1285
-
-
Menges, F.S.1
Craig, S.M.2
Tötsch, N.3
Bloomfield, A.4
Ghosh, S.5
Krüger, H.-J.6
Johnson, M.A.7
-
94
-
-
84962949654
-
-
Angew. Chem. 2016, 128, 1304–1307.
-
(2016)
Angew. Chem.
, vol.128
, pp. 1304-1307
-
-
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