Organic Letters
Letter
Part 1; Stella, V. J., Borchardt, R. T., Hageman, M. J., Oliyai, R., Maag,
H., Tilley, J. W., Eds.; Springer: New York, 2007; pp 703−729.
(3) For recent reviews, see: (a) Kielland, N.; Whiteoak, C. J.; Kleij,
A. W. Stereoselective Synthesis with Carbon Dioxide. Adv. Synth.
Catal. 2013, 355, 2115−2138. (b) Liu, Q.; Wu, L.; Jackstell, R.;
Beller, M. Using carbon dioxide as a building block in organic
synthesis. Nat. Commun. 2015, 6, 5933−5947. (c) Fujihara, T.; Tsuji,
Y. Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide
as the C1 source. Beilstein J. Org. Chem. 2018, 14, 2435−2460.
(d) Seo, H.; Nguyen, L. V.; Jamison, T. F. Using Carbon Dioxide as a
Building Block in Continuous Flow Synthesis. Adv. Synth. Catal. 2019,
361, 247−264. For selected examples, see: (e) Fujihara, T.; Nogi, K.;
Xu, T.; Terao, J.; Tsuji, Y. Nickel-Catalyzed Carboxylation of Aryl and
Vinyl Chlorides Employing Carbon Dioxide. J. Am. Chem. Soc. 2012,
134, 9106−9109. (f) Moragas, T.; Cornella, J.; Martin, R. Ligand-
Controlled Regiodivergent Ni-Catalyzed Reductive Carboxylation of
Allyl Esters with CO2. J. Am. Chem. Soc. 2014, 136, 17702−17705.
(g) Liu, Y.; Cornella, J.; Martin, R. Ni-Catalyzed Carboxylation of
Unactivated Primary Alkyl Bromides and Sulfonates with CO2. J. Am.
Chem. Soc. 2014, 136, 11212−11215. (h) Correa, A.; Leon, T.;
Martin, R. Ni-Catalyzed Carboxylation of C(sp2)- and C(sp3)-O
Bonds with CO2. J. Am. Chem. Soc. 2014, 136, 1062−1069. (i) Wang,
X.; Liu, Y.; Martin, R. Ni-Catalyzed Divergent Cyclization/
Carboxylation of Unactivated Primary and Secondary Alkyl Halides
with CO2. J. Am. Chem. Soc. 2015, 137, 6476−6479. (j) Nogi, K.;
Fujihara, T.; Terao, J.; Tsuji, Y. Cobalt- and Nickel-Catalyzed
Carboxylation of Alkenyl and Sterically Hindered Aryl Triflates
Electron Transfer-Electrosynthesis of Aromatic and α,β-Unsaturated
Carboxylic Acids from Carbon Dioxide. Eur. J. Org. Chem. 1998,
1998, 1811−1821.
(6) For recent reviews and examples of photoredox/transition metal
catalysis, see: (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) Fabry, D. C.; Rueping, M. Merging Visible Light Photoredox
Catalysis with Metal Catalyzed C-H Activations: On the Role of
Oxygen and Superoxide Ions as Oxidants. Acc. Chem. Res. 2016, 49,
1969−1979. (c) Hopkinson, M. N.; Tlahuext-Aca, A.; Glorius, F.
Merging Visible Light Photoredox and Gold Catalysis. Acc. Chem. Res.
2016, 49, 2261−2272. (d) Ye, Y.; Sanford, M. S. Merging Visible-
Light Photocatalysis and Transition-Metal Catalysis in the Copper-
Catalyzed Trifluoromethylation of Boronic Acids with CF3I. J. Am.
Chem. Soc. 2012, 134, 9034−9037. (e) Fabry, D. C.; Zoller, J.; Raja,
S.; Rueping, M. Combining Rhodium and Photoredox Catalysis for C-
H Functionalizations of Arenes: Oxidative Heck Reactions with
Visible Light. Angew. Chem., Int. Ed. 2014, 53, 10228−10231.
(f) Fabry, D. C.; Ronge, M. A.; Zoller, J.; Rueping, M. C-H.
Functionalization of Phenols Using Combined Ruthenium and
Photoredox Catalysis: In Situ Generation of the Oxidant. Angew.
Chem., Int. Ed. 2015, 54, 2801−2805. (g) Xie, J.; Zhang, T.; Chen, F.;
Mehrkens, N.; Rominger, F.; Rudolph, M.; Hashmi, A. S. K. Gold-
Catalyzed Highly Selective Photoredox C(sp2)-H Difluoroalkylation
and Perfluoroalkylation of Hydrazones. Angew. Chem., Int. Ed. 2016,
55, 2934−2938. (h) Xie, J.; Rudolph, M.; Rominger, F.; Hashmi, A. S.
K. Photoredox-Controlled Mono- and Di-Multifluoroarylation of
C(sp3)-H Bonds with Aryl Fluorides. Angew. Chem., Int. Ed. 2017, 56,
̈
Utilizing CO2. J. Org. Chem. 2015, 80, 11618−11623. (k) Borjesson,
M.; Moragas, T.; Martin, R. Ni-Catalyzed Carboxylation of
Unactivated Alkyl Chlorides with CO2. J. Am. Chem. Soc. 2016,
138, 7504−7507. (l) Rebih, F.; Andreini, M.; Moncomble, A.;
Harrison-Marchand, A.; Maddaluno, J.; Durandetti, M. Direct
Carboxylation of Aryl Tosylates by CO2 Catalyzed by In situ-
Generated Ni0. Chem. - Eur. J. 2016, 22, 3758−3763. (m) Moragas,
T.; Gaydou, M.; Martin, R. Nickel-Catalyzed Carboxylation of
Benzylic C-N Bonds with CO2. Angew. Chem., Int. Ed. 2016, 55,
5053−5057. (n) Li, Y.; Cui, X.; Dong, K.; Junge, K.; Beller, M.
Utilization of CO2 as a C1 Building Block for Catalytic Methylation
Reactions. ACS Catal. 2017, 7, 1077−1086.
̈
7266−7270. (i) Marzo, L.; Pagire, S. K.; Reiser, O.; Konig, B. Visible-
Light Photocatalysis: Does It Make a Difference in Organic Synthesis?
Angew. Chem., Int. Ed. 2018, 57, 10034−10072. (j) Yue, H.; Zhu, C.;
Rueping, M. Cross-Coupling of Sodium Sulfinates with Aryl,
Heteroaryl, and Vinyl Halides by Nickel/Photoredox Dual Catalysis.
Angew. Chem., Int. Ed. 2018, 57, 1371−1375. (k) Zheng, J.; Breit, B.
Regiodivergent Hydroaminoalkylation of Alkynes and Allenes by a
Combined Rhodium and Photoredox Catalytic System. Angew. Chem.,
Int. Ed. 2019, 58, 3392−3397. (l) Kalyani, D.; McMurtrey, K. B.;
Neufeldt, S. R.; Sanford, M. S. Room-Temperature C-H Arylation:
Merger of Pd-Catalyzed C-H Functionalization and Visible-Light
Photocatalysis. J. Am. Chem. Soc. 2011, 133, 18566−18569. (m) Shu,
X.-Z.; Zhang, M.; He, Y.; Frei, H.; Toste, F. D. Dual Visible Light
Photoredox and Gold-Catalyzed Arylative Ring Expansion. J. Am.
Chem. Soc. 2014, 136, 5844−5847. (n) Tellis, J. C.; Primer, D. N.;
Molander, G. A. Dual catalysis. Single-electron transmetalation in
organoboron cross-coupling by photoredox/nickel dual catalysis.
Science 2014, 345, 433−436. (o) Noble, A.; McCarver, S. J.;
MacMillan, D. W. C. Merging Photoredox and Nickel Catalysis:
Decarboxylative Cross-Coupling of Carboxylic Acids with Vinyl
Halides. J. Am. Chem. Soc. 2015, 137, 624−627. (p) Lang, S. B.;
O’Nele, K. M.; Tunge, J. A. Decarboxylative Allylation of Amino
Alkanoic Acids and Esters via Dual Catalysis. J. Am. Chem. Soc. 2014,
136, 13606−13609. (q) Tasker, S. Z.; Jamison, T. F. Highly
Regioselective Indoline Synthesis under Nickel/Photoredox Dual
Catalysis. J. Am. Chem. Soc. 2015, 137, 9531−9534. (r) Huang, H.;
Jia, K.; Chen, Y. Radical Decarboxylative Functionalizations Enabled
by Dual Photoredox Catalysis. ACS Catal. 2016, 6, 4983−4988.
(4) For recent reviews, see: (a) Zhang, L.; Hou, Z. N -Heterocyclic
carbine (NHC)−copper-catalysed transformations of carbon dioxide.
́
́
Chem. Sci. 2013, 4, 3395−3403. (b) Tortajada, A.; Julia-Hernandez,
F.; Borjesson, M.; Moragas, T.; Martin, R. Transition-Metal-Catalyzed
Carboxylation Reactions with Carbon Dioxide. Angew. Chem., Int. Ed.
2018, 57, 15948−15982. (c) Hou, J.; Li, J.-S.; Wu, J. Recent
Development of Light-Mediated Carboxylation Using CO2 as the
Feedstock. Asian J. Org. Chem. 2018, 7, 1439−1447. For recent
selected catalytic carboxylation examples, see: (d) Fujihara, T.; Xu, T.;
Semba, K.; Terao, J.; Tsuji, Y. Copper-Catalyzed Hydrocarboxylation
of Alkynes Using CarbonDioxide and Hydrosilanes. Angew. Chem., Int.
Ed. 2011, 50, 523−527. (e) Mizuno, H.; Takaya, J.; Iwasawa, N.
Rhodium(I)-Catalyzed Direct Carboxylation of Arenes with CO2 via
Chelation-Assisted C−H Bond Activation. J. Am. Chem. Soc. 2011,
133, 1251−1253. (f) Li, S.; Yuan, W.; Ma, S. Highly Regio- and
Stereoselective Three-Component Nickel-Catalyzedsyn-Hydrocarbox-
ylation of Alkynes with Diethyl Zinc and CarbonDioxide. Angew.
Chem., Int. Ed. 2011, 50, 2578−2582. (g) Sasano, K.; Takaya, J.;
Iwasawa, N. Palladium(II)-Catalyzed Direct Carboxylation of Alkenyl
C-H Bonds with CO2. J. Am. Chem. Soc. 2013, 135, 10954−10957.
(s) Schwarz, J. L.; Schafers, F.; Tlahuext-Aca, A.; Luckemeier, L.;
̈
Glorius, F. Diastereoselective Allylation of Aldehydes by Dual
Photoredox and Chromium Catalysis. J. Am. Chem. Soc. 2018, 140,
12705−12709. (t) Liao, L.-L.; Gui, Y.-Y.; Zhang, X.-B.; Shen, G.; Liu,
H.-D.; Zhou, W.-J.; Li, J.; Yu, D.-G. Phosphorylation of Alkenyl and
Aryl C-O Bonds via Photoredox/Nickel Dual Catalysis. Org. Lett.
2017, 19, 3735−3738. (u) Liu, N.-W.; Hofman, K.; Herbert, A.;
Manolikakes, G. Visible-Light Photoredox/Nickel Dual Catalysis for
the Cross-Coupling of Sulfinic Acid Salts with Aryl Iodides. Org. Lett.
2018, 20, 760−763. (v) Matsui, J. K.; Molander, G. A. Direct α-
Arylation/Heteroarylation of 2-Trifluoroboratochromanones via
Photoredox/Nickel Dual Catalysis. Org. Lett. 2017, 19, 436−439.
́
(h) Leon, T.; Correa, A.; Martin, R. Ni-Catalyzed Direct
Carboxylation of Benzyl Halides with CO2. J. Am. Chem. Soc. 2013,
135, 1221−1224. (i) Mita, T.; Higuchi, Y.; Sato, Y. Highly
Regioselective Palladium-Catalyzed Carboxylation of Allylic Alcohols
with CO2. Chem. - Eur. J. 2015, 21, 16391−16394.
(5) For electrochemical carboxylation, see: (a) Amatore, C.; Jutand,
A.; Khalil, F.; Nielsen, M. F. Carbon Dioxide as a C1 Building Block.
Mechanism of Palladium-Catalyzed Carboxylation of Aromatic
Halides. J. Am. Chem. Soc. 1992, 114, 7076−7085. (b) Jutand, A.;
́
Negri, S. Activation of Aryl and Vinyl Triflates by Palladium and
E
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