ACS Catalysis
Page 14 of 15
Y.; Zhao, H.; Hartwig, J. F. Cooperative Tandem Catalysis by an
Strategy for Indole Synthesis via Intramolecular C-C Bond
1
2
3
4
5
6
7
8
Organometallic Complex and a Metalloenzyme. Angew. Chem. Int.
Ed. 2014, 53, 465–469. (c) Denard, C. A.; Bartlett, M. J.; Wang, Y.;
Lu, L.; Hartwig, J. F.; Zhao, H. Development of a One-Pot Tandem
Reaction Combining Ruthenium-Catalyzed Alkene Metathesis and
Enantioselective Enzymatic Oxidation to Produce Aryl Epoxides.
ACS Catal. 2015, 5, 3817–3822. (d) Latham, J.; Henry, J. M.; Sharif,
H. H.; Menon, B. R.; Shepherd, S. A.; Greaney, M. F.; Micklefield, J.
Integrated Catalysis Opens New Arylation Pathways via
Regiodivergent Enzymatic C–H Activation. Nat. Commun. 2016, 7,
11873. (e) Litman, Z. C.; Wang, Y.; Zhao, H.; Hartwig, J. F.
Cooperative Asymmetric Reactions Combining Photocatalysis and
Enzymatic Catalysis. Nature 2018, 560, 355. (f) Cosgrove, S. C.;
Hussain, S.; Turner, N. J.; Marsden, S. P. Synergistic
Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines.
ACS Catal. 2018, 8, 5570–5573.
Construction under Visible Light Irradiation: Cross-Coupling
Hydrogen Evolution Reaction. ACS Catal. 2016, 6, 4635−4639 (d)
Hu, X.; Zhang, G.; Bu, F.; Luo, X.; Yi, K.; Zhang, H.; Lei, A.
Photoinduced Oxidative Activation of Electron-Rich Arenes:
Alkenylation with H2 Evolution under External Oxidant-Free
Conditions. Chem. Sci. 2018, 9, 1521−1526. (e) Tang, S.; Zeng, L;
Lei, A. Oxidative R1–H/R2–H Cross-Coupling with Hydrogen
Evolution. J. Am. Chem. Soc. 2018, 140, 13128−13135. (f) Wang, H.;
Gao, X.; Lv, Z.; Abdelilah, T.; Lei, A. Recent Advances in Oxidative
R1−H/R2−H Cross-Coupling with Hydrogen Evolution via Photo-
/Electrochemistry. Chem. Rev. 2019, 119, 6769−6787.
(19) Blanksby, S. J.; Ellison, G. B. Bond Dissociation Energies of
Organic Molecules. Acc. Chem. Res. 2003, 36, 255–263.
(20) Noyori, R.; Kato, M.; Kawanisi, M.; Nozaki, H.
Photochemical Reaction of Benzopyridines with Alkanoic Acids
Novel Reductive Alkylation of Acridine, Quinoline and Isoquinoline
under Decarboxylation. Tetrahedron 1969, 25, 1125−1136.
(21) Liu, X.; Karsili, T. N.; Sobolewski, A. L.; Domcke, W.
Photocatalytic Water Splitting with the Acridine Chromophore: A
Computational Study. J. Phys. Chem. B. 2015, 119, 10664−10672.
(22) (a) Inokuchi, T.; Tsuji, M.; Kawafuchi, H.; Torii, S. Indirect
electroreduction of 2-Alkyl-2-(bromomethyl)cycloalkanones with
Cobaloxime to Form 3-Alkyl-2-alkenones via 1,2-Acyl Migration. J.
Org. Chem. 1991, 56, 5945–5948. (b) West, J. G.; Huang, D.;
Sorensen, E. J. Acceptorless Dehydrogenation of Small Molecules
Through Cooperative Base Metal Catalysis. Nat. Commun. 2015, 6,
10093. (c) Abrams, D. J.; West, J. G.; Sorensen, E. J. Toward a Mild
Dehydroformylation Using Base-Metal Catalysis. Chem. Sci. 2017, 8,
1954–1959. (d) Cao, H.; Jiang, H.; Feng, H.; Kwan, J. M. C.; Liu, X.;
Wu, J. Photo-induced Decarboxylative Heck-Type Coupling of
Unactivated Aliphatic Acids and Terminal Alkenes in the Absence of
Sacrificial Hydrogen Acceptors. J. Am. Chem. Soc. 2018, 140,
16360–16367.
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
(11) Bacha, J. D.; Kochi, J. K. Alkenes from Acids by Oxidative
Decarboxylation. Tetrahedron 1968, 24, 2215–2226.
(12) (a) Liu, Y.; Kim, K. E.; Herbert, M. B.; Fedorov, A.; Grubbs, R.
H.; Stoltz, B. M. Palladium‐Catalyzed Decarbonylative Dehydration
of Fatty Acids for the Production of Linear Alpha Olefins. Adv. Synth.
Catal. 2014, 356, 130–136. (b) Miranda, M. O.; Pietrangelo, A.;
Hillmyer, M. A.; Tolman, W. B. Catalytic Decarbonylation of
Biomass-Derived Carboxylic Acids as Efficient Route to Commodity
Monomers. Green Chem. 2012, 14, 490–494. (c) Chatterjee, A.;
Hopen Eliasson, S. H.; Törnroos, K. W.; Jensen, V. R. 2016,
Palladium Precatalysts for Decarbonylative Dehydration of Fatty
Acids to Linear -Olefins. ACS Catal. 2012, 6, 7784–7789. (d) Liu,
Y.; Virgil, S. C.; Grubbs, R. H.; Stoltz, B. M. Palladium‐Catalyzed
Decarbonylative Dehydration for the Synthesis of ‐Vinyl Carbonyl
Compounds and Total Synthesis of (−)‐Aspewentins A, B, and C.
Angew. Chem. Int. Ed. 2015, 54, 11800–11803. (e) Chatterjee, A.;
Eliasson, S. H. H.; Jensen, V. R. Selective Production of Linear -
Olefins via Catalytic Deoxygenation of Fatty Acids and Derivatives.
Catal. Sci. Technol. 2018, 8, 1487–1499. (f) Zhang, X.; Jordan, F.;
Szostak, M. Transition-Metal-Catalyzed Decarbonylation of
Carboxylic Acids to Olefins: Exploiting Acyl C–O Activation for the
Production of High Value Products. Org. Chem. Front. 2018, 5,
2515–2521. (g) Shang, R., Leu, L. Sci. China Chem. 2011, 54, 1670–
1687.
(13) Tlahuext-Aca, A.; Candish, L.; Garza-Sanchez, R. A.; Glorius,
F. Decarboxylative Olefination of Activated Aliphatic Acids Enabled
by Dual Organophotoredox/Copper Catalysis. ACS Catal. 2018, 8,
1715–1719.
(14) Cheng, W. M.; Shang, R.; Fu, Y. Irradiation-Induced
Palladium-Catalyzed Decarboxylative Desaturation Enabled by a
Dual Ligand System. Nature Commun. 2018, 9, 5215.
(15) Sun, X.; Chen, J.; Ritter, T. Catalytic Dehydrogenative
Decarboxyolefination of Carboxylic Acids. Nat. Chem. 2018, 10,
1229–1233.
(16) (a) Cartwright, K. C.; Tunge, J. A. Decarboxylative
Elimination of N-Acyl Amino Acids via Photoredox/Cobalt Dual
Catalysis. ACS Catal. 2018, 8, 11801–11806. (b) Cartwright, K. C.;
Lang, S. B.; Tunge, J. A. Photoinduced Kochi Decarboxylative
Elimination for the Synthesis of Enamides and Enecarbamates from
N-Acyl Amino Acids. J. Org. Chem. 2019, 84, 2933−2940.
(17) Green, S. A.; Crossley, S. W. M.; Matos, J. L. M.; Vásquez-
Céspedes, S.; Shevick, S. L.; Shenvi, R. A. The High Chemofidelity
of Metal-Catalyzed Hydrogen Atom Transfer. Acc. Chem. Res. 2018,
51, 2628−2640.
(18) (a) Meng, Q. -Y.; Zhong, J. -J.; Liu, Q.; Gao, X. -W.; Zhang,
H. -H.; Lei, T.; Li, Z.-J.; Feng, K.; Chen, B.; Tung, C. -H.; Wu, L. -Z.
A Cascade Cross-Coupling Hydrogen Evolution Reaction by Visible
Light Catalysis. J. Am. Chem. Soc. 2013, 135, 19052–19055. (b)
Zhang, G.; Liu, C.; Yi, H.; Meng, Q.; Bian, C.; Chen, H.; Jian, J.X.;
Wu, L. Z.; Lei, A. External Oxidant-Free Oxidative Cross-Coupling:
(23) (a) Pines, E.; Huppert, D.; Gutman, M.; Nachliel, N.; Fishman,
M. The pOH Jump: Determination of Deprotonation Rates of Water
by 6-Methoxyquinoline and Acridine. J. Phys. Chem. 1986, 90, 6366–
6370. (b) Ireland, J. F.; Wyatt, P. A. H. Acid-Base Properties of
Electronically Excited States of Organic Molecules. Adv. Phys. Org.
Chem. 1976, 12, 131–221.
(24) (a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. Visible
Light Photoredox Catalysis with Transition Metal Complexes:
Applications in Organic Synthesis. Chem. Rev. 2013, 113, 5322–
5363. (b) Romero, N. A.; Nicewicz, D. A. Organic photoredox
catalysis. Chem. Rev. 2016, 116, 10075–10166. (c) Griffin, J. D.;
Zeller, M. A.; Nicewicz, D. A. Hydrodecarboxylation of Carboxylic
and Malonic Acid Derivatives via Organic Photoredox Catalysis:
Substrate Scope and Mechanistic Insight. J. Am. Chem. Soc. 2015,
137, 11340−11348. (d) Narayanam, J. M.; Stephenson, C. R. Visible
Light Photoredox Catalysis: Applications in Organic Synthesis.
Chem. Soc. Rev. 2011, 40, 102–113. (e) Yoon, T. P.; Ischay, M. A.;
Du, J. Visible Light Photocatalysis as a Greener Approach to
Photochemical Synthesis. Nat. Chem. 2010, 2, 527. For an alternative
photocatalytic system based on Ph3P/NaI, see: (f) Fu, M.-C.; Shang,
R.; Zhao, B.; Wang, B.; Fu, Y. Photocatalytic Decarboxylative
Alkylations Mediated by Triphenylphosphine and Sodium Iodide.
Science 2019, 363, 1429−1434.
(25) Schmidt, A.; Liu, M. Recent Advances in the Chemistry of
Acridines. Adv. Heterocycl. Chem. 2015, 115, 287–353.
(26) (a) Hall, D. G. Boronic Acids; Wiley-VCH: Weinheim,
Germany, 2011. (b) Nguyen, V. D.; Nguyen, V. T.; Jin, S.; Dang, H.
T.; Larionov, O. V. Organoboron Chemistry Comes to Light: Recent
Advances in Photoinduced Synthetic Approaches to Organoboron
Compounds. Tetrahedron 2019, 75, 584–602.
(27) Fockink, D. H.; Mise, K. M.; Zarbin, P. H. Male-produced Sex
Pheromone of the Carrion Beetles, Oxelytrum discicolle and Its
Attraction to Food Sources. J. Chem. Ecol. 2013, 39, 1056–1065.
(28) (a) Dempsey, J. L.; Brunschwig, B. S.; Winkler, J. R.; Gray,
H. B. Hydrogen Evolution Catalyzed by Cobaloximes. Acc. Chem.
Res. 2009, 42, 1995–2004. (b) Dalle, K. E.; Warnan, J.; Leung, J. J.;
a
Photoredox Cobalt-Catalyzed Aromatic C–H Thiolation for
Constructing C–S Bonds. J. Am. Chem. Soc. 2015, 137, 9273–9280.
(c) Wu, C. -J.; Meng, Q. -Y.; Lei, T.; Zhong, J. -J.; Liu, W. -Q.; Zhao,
L. -M.; Li, Z. -J.; Chen, B.; Tung, C. -H.; Wu, L. -Z. An Oxidant-Free
14
ACS Paragon Plus Environment