Page 9 of 10
Journal of the American Chemical Society
Racemization Catalyst. Chem. Eur. J. 2017, 23, 1048-1051; (l) Del
Allylic Alcohols. Angew. Chem. Int. Ed. 2013, 52, 12883-12887; (b)
Roudier, M.; Constantieux, T.; Quintard, A.; Rodriguez, J.
Enantioselective Cascade Formal Reductive Insertion of Allylic Alcohols
into the C(O)–C Bond of 1,3-Diketones: Ready Access to Synthetically
Valuable 3-Alkylpentanol Units. Org. Lett. 2014, 16, 2802-2805; (c)
Quintard, A.; Rodriguez, J. Catalytic Enantioselective OFF-ON Activation
Processes Initiated by Hydrogen Transfer: Concepts and Challenges.
Chem. Commun. 2016, 52, 10456-10473; (d) Roudier, M.; Constantieux,
T.; Quintard, A.; Rodriguez, J. Triple Iron/Copper/Iminium Activation for
the Efficient Redox Neutral Catalytic Enantioselective Functionalization
of Allylic Alcohols. ACS Catal. 2016, 6, 5236-5244.
Grosso, A.; Chamberlain, A. E.; Clarkson, G. J.; Wills, M. Synthesis and
Applications to Catalysis of Novel Cyclopentadienone Iron Tricarbonyl
Complexes. Dalton Trans. 2018, 47, 1451-1470.
1
2
3
4
5
6
7
8
(16) (a) Trovitch, R. J.; Lobkovsky, E.; Bill, E.; Chirik, P. J. Functional
Group Tolerance and Substrate Scope in Bis(imino)pyridine Iron
Catalyzed Alkene Hydrogenation. Organometallics 2008, 27, 1470-1478;
(b) Yu, R. P.; Darmon, J. M.; Hoyt, J. M.; Margulieux, G. W.; Turner, Z.
R.; Chirik, P. J. High-Activity Iron Catalysts for the Hydrogenation of
Hindered, Unfunctionalized Alkenes. ACS Catal. 2012, 2, 1760-1764; (c)
Chirik, P. J. Iron- and Cobalt-Catalyzed Alkene Hydrogenation: Catalysis
with Both Redox-Active and Strong Field Ligands. Acc. Chem. Res. 2015,
48, 1687-1695; (d) Bornschein, C.; Werkmeister, S.; Wendt, B.; Jiao, H.;
Alberico, E.; Baumann, W.; Junge, H.; Junge, K.; Beller, M. Mild and
Selective Hydrogenation of Aromatic and Aliphatic (di)Nitriles with A
Well-defined Iron Pincer Complex. Nat. Commun. 2014, 5, 4111; (e)
Chakraborty, S.; Brennessel, W. W.; Jones, W. D. A Molecular Iron
Catalyst for the Acceptorless Dehydrogenation and Hydrogenation of N-
Heterocycles. J. Am. Chem. Soc. 2014, 136, 8564-8567; (f) Chakraborty,
S.; Dai, H.; Bhattacharya, P.; Fairweather, N. T.; Gibson, M. S.; Krause, J.
A.; Guan, H. Iron-Based Catalysts for the Hydrogenation of Esters to
Alcohols. J. Am. Chem. Soc. 2014, 136, 7869-7872; (g) Chakraborty, S.;
Lagaditis, P. O.; Förster, M.; Bielinski, E. A.; Hazari, N.; Holthausen, M.
C.; Jones, W. D.; Schneider, S. Well-Defined Iron Catalysts for the
Acceptorless Reversible Dehydrogenation-Hydrogenation of Alcohols and
Ketones. ACS Catal. 2014, 4, 3994-4003; (h) Gorgas, N.; Stöger, B.;
Veiros, L. F.; Pittenauer, E.; Allmaier, G.; Kirchner, K. Efficient
Hydrogenation of Ketones and Aldehydes Catalyzed by Well-Defined
Iron(II) PNP Pincer Complexes: Evidence for an Insertion Mechanism.
Organometallics 2014, 33, 6905-6914; (i) Bonitatibus, P. J.; Chakraborty,
S.; Doherty, M. D.; Siclovan, O.; Jones, W. D.; Soloveichik, G. L.
Reversible Catalytic Dehydrogenation of Alcohols for Energy Storage.
Proc. Nat. Acad. Sci. 2015, 112, 1687-1692; (j) Glüer, A.; Förster, M.;
Celinski, V. R.; Schmedt auf der Günne, J.; Holthausen, M. C.; Schneider,
S. Highly Active Iron Catalyst for Ammonia Borane Dehydrocoupling at
Room Temperature. ACS Catal. 2015, 5, 7214-7217; (k) Zell, T.; Ben-
David, Y.; Milstein, D. Highly Efficient, General Hydrogenation of
Aldehydes Catalyzed by PNP Iron Pincer Complexes. Catal. Sci. Technol.
2015, 5, 822-826; (l) Zell, T.; Milstein, D. Hydrogenation and
Dehydrogenation Iron Pincer Catalysts Capable of Metal–Ligand
Cooperation by Aromatization/Dearomatization. Acc. Chem. Res. 2015,
48, 1979-1994; (m) Bertini, F.; Gorgas, N.; Stöger, B.; Peruzzini, M.;
Veiros, L. F.; Kirchner, K.; Gonsalvi, L. Efficient and Mild Carbon
Dioxide Hydrogenation to Formate Catalyzed by Fe(II) Hydrido Carbonyl
Complexes Bearing 2,6-(Diaminopyridyl)diphosphine Pincer Ligands.
ACS Catal. 2016, 6, 2889-2893; (n) Rezayee, N. M.; Samblanet, D. C.;
Sanford, M. S. Iron-Catalyzed Hydrogenation of Amides to Alcohols and
Amines. ACS Catal. 2016, 6, 6377-6383; (o) Xu, R.; Chakraborty, S.;
Bellows, S. M.; Yuan, H.; Cundari, T. R.; Jones, W. D. Iron-Catalyzed
Homogeneous Hydrogenation of Alkenes under Mild Conditions by a
Stepwise, Bifunctional Mechanism. ACS Catal. 2016, 6, 2127-2135; (p)
Zirakzadeh, A.; Kirchner, K.; Roller, A.; Stöger, B.; Widhalm, M.; Morris,
R. H. Iron(II) Complexes Containing Chiral Unsymmetrical PNP′ Pincer
Ligands: Synthesis and Application in Asymmetric Hydrogenations.
Organometallics 2016, 35, 3781-3787; (q) Chakraborty, S.; Leitus, G.;
Milstein, D. Iron-Catalyzed Mild and Selective Hydrogenative Cross-
Coupling of Nitriles and Amines To Form Secondary Aldimines. Angew.
Chem. Int. Ed. 2017, 56, 2074-2078; (r) Karunananda, M. K.; Mankad, N.
P. Cooperative Strategies for Catalytic Hydrogenation of Unsaturated
Hydrocarbons. ACS Catal. 2017, 7, 6110-6119.
(19) (a) Lelais, G.; MacMillan, D. W. C. Modern Strategies in Organic
Catalysis: The Advent and Development of Iminium Activation.
Aldrichimica Acta 2006, 39, 79-87; (b) MacMillan, D. W. C. The Advent
and Development of Organocatalysis. Nature 2008, 455, 304.
9
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
(20) (a) Hamid, M. H. S. A.; Slatford, P. A.; Williams, J. M. J.
Borrowing Hydrogen in the Activation of Alcohols. Adv. Synth. Catal.
2007, 349, 1555-1575; (b) Guillena, G.; J. Ramón, D.; Yus, M. Hydrogen
Autotransfer in the N-Alkylation of Amines and Related Compounds
using Alcohols and Amines as Electrophiles. Chem. Rev. 2009, 110, 1611-
1641; (c) Nixon, T. D.; Whittlesey, M. K.; Williams, J. M. J. Transition
Metal Catalysed Reactions of Alcohols Using Borrowing Hydrogen
Methodology. Dalton Trans. 2009, 753-762; (d) Dobereiner, G. E.;
Crabtree, R. H. Dehydrogenation as a Substrate-Activating Strategy in
Homogeneous Transition-Metal Catalysis. Chem. Rev. 2010, 110, 681-
703; (e) Watson, A. J. A.; Williams, J. M. J. The Give and Take of
Alcohol Activation. Science 2010, 329, 635-636; (f) Choi, J.; MacArthur,
A. H. R.; Brookhart, M.; Goldman, A. S. Dehydrogenation and Related
Reactions Catalyzed by Iridium Pincer Complexes. Chem. Rev. 2011, 111,
1761-1779; (g) Gunanathan, C.; Milstein, D. Applications of Acceptorless
Dehydrogenation and Related Transformations in Chemical Synthesis.
Science 2013, 341, 1229712; (h) Obora, Y. Recent Advances in α-
Alkylation Reactions using Alcohols with Hydrogen Borrowing
Methodologies. ACS Catal. 2014, 4, 3972-3981; (i) Nandakumar, A.;
Midya, S. P.; Landge, V. G.; Balaraman, E. Transition-Metal-Catalyzed
Hydrogen-Transfer Annulations: Access to Heterocyclic Scaffolds.
Angew. Chem. Int. Ed. 2015, 54, 11022-11034; (j) Werkmeister, S.;
Neumann, J.; Junge, K.; Beller, M. Pincer-Type Complexes for Catalytic
(De)Hydrogenation and Transfer (De)Hydrogenation Reactions: Recent
Progress. Chem. Eur. J. 2015, 21, 12226-12250; (k) Yang, Q.; Wang, Q.;
Yu, Z. Substitution of Alcohols by N-Nucleophiles via Transition Metal-
catalyzed Dehydrogenation. Chem. Soc. Rev. 2015, 44, 2305-2329; (l)
Quintard, A.; Rodriguez, J. A Step into an eco-Compatible Future: Iron-
and
Cobalt-catalyzed
Borrowing
Hydrogen
Transformation.
Chemsuschem 2016, 9, 28-30; (m) Feng, J.; Kasun, Z. A.; Krische, M. J.
Enantioselective Alcohol C–H Functionalization for Polyketide
Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal
Chemical Synthesis. J. Am. Chem. Soc. 2016, 138, 5467-5478; (n)
Crabtree, R. H. Homogeneous Transition Metal Catalysis of Acceptorless
Dehydrogenative Alcohol Oxidation: Applications in Hydrogen Storage
and to Heterocycle Synthesis. Chem. Rev. 2017, 117, 9228-9246; (o)
Wang, C.; Xiao, J. Iridacycles for Hydrogenation and Dehydrogenation
Reactions. Chem. Commun. 2017, 53, 3399-3411; (p) Corma, A.; Navas,
J.; Sabater, M. J. Advances in One-Pot Synthesis through Borrowing
Hydrogen Catalysis. Chem. Rev. 2018, 118, 1410-1459.
(21) Emayavaramban, B.; Roy, M.; Sundararaju, B. Iron-Catalyzed
Allylic Amination Directly from Allylic Alcohols. Chem. Eur. J. 2016, 22,
3952-3955.
(22) (a) Huehls, C. B.; Lin, A.; Yang, J. Iron-Catalyzed Intermolecular
Hydroamination of Styrenes. Org. Lett. 2014, 16, 3620-3623; (b) Gui, J.;
Pan, C.-M.; Jin, Y.; Qin, T.; Lo, J. C.; Lee, B. J.; Spergel, S. H.;
Mertzman, M. E.; Pitts, W. J.; La Cruz, T. E.; Schmidt, M. A.; Darvatkar,
N.; Natarajan, S. R.; Baran, P. S. Practical Olefin Hydroamination with
Nitroarenes. Science 2015, 348, 886-891.
(17) (a) Mastalir, M.; Glatz, M.; Gorgas, N.; Stöger, B.; Pittenauer, E.;
Allmaier, G.; Veiros, L. F.; Kirchner, K. Divergent Coupling of Alcohols
and Amines Catalyzed by Isoelectronic Hydride MnI and FeII PNP Pincer
Complexes. Chem. Eur. J. 2016, 22, 12316-12320; (b) Mastalir, M.;
Stöger, B.; Pittenauer, E.; Puchberger, M.; Allmaier, G.; Kirchner, K. Air
Stable Iron(II) PNP Pincer Complexes as Efficient Catalysts for the
Selective Alkylation of Amines with Alcohols. Adv. Synth. Catal. 2016,
358, 3824-3831; (c) Reed-Berendt, B. G.; Polidano, K.; Morrill, L. C.
Recent Advances in Homogeneous Borrowing Hydrogen Catalysis Using
Earth-abundant First Row Transition Metals. Org. Biomol. Chem. 2019,
17, 1595-1607; (d) Irrgang, T.; Kempe, R. 3d-Metal Catalyzed N- and C-
Alkylation Reactions via Borrowing Hydrogen or Hydrogen Autotransfer.
Chem. Rev. 2019, 119, 2524-2549.
(23) Gurak, J. A.; Yang, K. S.; Liu, Z.; Engle, K. M. Directed,
Regiocontrolled Hydroamination of Unactivated Alkenes via
Protodepalladation. J. Am. Chem. Soc. 2016, 138, 5805-5808.
(24) (a) Petersson, M. J.; Jenkins, I. D.; Loughlin, W. A. The Use of
Phosphonium Anhydrides for the Synthesis of 2-Oxazolines, 2-
Thiazolines and 2-Dihydrooxazine under Mild Conditions. Org. Biomol.
Chem. 2009, 7, 739-746; (b) Mollo, M. C.; Orelli, L. R. Microwave-
Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines,
and 4,5,6,7-Tetrahydro-1,3-oxazepines. Org. Lett. 2016, 18, 6116-6119.
(25) (a) Obligacion, J. V.; Chirik, P. J. Highly Selective
Bis(imino)pyridine Iron-Catalyzed Alkene Hydroboration. Org. Lett.
(18) (a) Quintard, A.; Constantieux, T.; Rodriguez, J. An Iron/Amine-
Catalyzed Cascade Process for the Enantioselective Functionalization of
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