The Journal of Organic Chemistry
Page 12 of 13
(b) Romero, N. A.; Nicewicz, D. A. Organic Photoredox (12) Singh, R.; Allam, B. K.; Singh, N.; Kumari, K.; Singh S.
Catalysis. Chem. Rev. 2016, 116, 10075.
K.; Singh, K. N. A Direct Metal-Free Decarboxylative Sulfono
Functionalization (DSF) of Cinnamic Acids to α, β-
Unsaturated Phenyl Sulfones. Org. Lett. 2015, 17, 2656.
(13) Cai, S.; Xu, Y.; Chen, D.; Li, L.; Chen, Q.; Huang, M.;
1
2
3
4
5
6
7
8
(7) Fawcett,A.; Pradeilles, J.; Wang, Y.; Mutsuga, T.; Myers
,E. L.; Aggarwal,V. K. Photoinduced Decarboxylative
Borylation of Carboxylic Acids. Science 2017, 357, 283.
(8) (a) Alba, A.-N. R.; Companyó, X.; Rios, R. Sulfones: New
Reagents in Organocatalysis. Chem. Soc. Rev. 2010, 39, 2018.
(b) Back, T. G.; Clary, K. N.; Gao, D. Cycloadditions and
Cyclizations of Acetylenic, Allenic, and Conjugated Dienyl
Sulfones. Chem. Rev. 2010, 110, 4498.
(9) (a) Nishimura, T.; Takiguchi, Y.; Hayashi, T. Effect of
Chiral Diene Ligands in Rhodium-Catalyzed Asymmetric
Addition of Arylboronic Acids to α, β-Unsaturated Sulfonyl
Compounds. J. Am. Chem. Soc. 2012, 134, 9086. (b) Yoshida,
K.; Hayashi, T. A New cine-Substitution of Alkenyl Sulfones
with Aryltitanium Reagents Catalyzed by Rhodium:
Mechanistic Studies and Catalytic Asymmetric Synthesis of
Allylarenes. J. Am. Chem. Soc. 2003, 125, 2872.
(10) (a) Baskin, J. M.; Wang, Z. An Efficient Copper Catalyst
for the Formation of Sulfones from Sulfinic Acid Salts and
Aryl Iodides. Org. Lett. 2002, 4, 4423. (b) Matteucci, M.;
Bhalay ,G.; Bradley, M. Mild and Highly Chemoselective
Oxidation of Thioethers Mediated by Sc(OTf)3. Org. Lett.
2003, 5, 235. (c) Cacchi, S.; Fabrizi, G.; Goggiamani, A.;
Parisi, L. M.; Bernini, R. Unsymmetrical Diaryl Sulfones and
Aryl Vinyl Sulfones through Palladium-Catalyzed Coupling of
Aryl and Vinyl Halides or Triflates with Sulfinic Acid Salts. J.
Org. Chem. 2004, 69, 5608. (d) Chawla, R.; Kapoor, R.; Singh,
A. K.; Yadav, L. D. S. A One-Pot Regioselective Synthetic
Route to Vinyl Sulfones from Terminal Epoxides in Aqueous
Media. Green Chem. 2012, 14, 1308. (e) Balaji V, R.;
Kandikere Ramaiah, P. Copper-catalyzed decarboxylative
sulfonylation of α,β-unsaturated carboxylic acids. J. Org.
Chem. 2014, 79, 8110. (f) Xiang, J.; Deng, W.; Xue, N.; Guo,
R.; Tu, X.; Luo, W. Efficient Synthesis of Vinyl Sulfones by
Manganese-Catalyzed Decarboxylative Coupling of Cinnamic
Acids with Aromatic Sulfinic Acid Sodium Salts. Synlett.
2016, 27, 2695-2698. (g) Cai, S.-Y.; Chen, D.-L.; Xu, Y.-H.;
Weng, W.; Li, L.-H.; Zhang, R.-J.; Huang, M.-Q. Visible-
Light-Promoted Syntheses of β-Keto Sulfones from Alkynes
and Sulfonylhydrazides. Org. Biomol. Chem. 2016, 14, 4205.
(h) Kadari, L.; Palakodety, R. K.; Yallapragada, L. P. Iodine-
Catalyzed Facile Approach to Sulfones Employing TosMIC as
a Sulfonylating Agent. Org. Lett. 2017, 19, 2580-2583. (i)
Zhao, Y.; Lai, Y. L.; Du, K. S.; Lin, D. Z.; Huang, J. M.
Electrochemical Decarboxylative Sulfonylation of Cinnamic
Acids with Aromatic Sulfonylhydrazides to Vinyl Sulfones. J.
Org. Chem. 2017, 82, 9655-9661. (j) Ratushnyy, M.;
Weng,
W.,
Visible-Light-Enabled
Decarboxylative
Sulfonylation of Cinnamic Acids with Sulfonylhydrazides
under Transition-Metal-Free Conditions. Org. Lett. 2016, 18,
2990.
(14) (a) Xuan, J.; Studer, A. Radical Cascade Cyclization of
1,n-Enynes and Diynes for the Synthesis of Carbocycles and
Heterocycles. Chem. Soc. Rev. 2017, 46, 4329. (b) Cao, X.;
Cheng, X.; Xuan, J. Arylsulfonyl Radical Triggered 1,6-Enyne
Cyclization: Synthesis of γ-Lactams Containing Alkenyl C–X
Bonds. Org. Lett. 2018, 20, 449. (c) Cao, X; Cai, B.-G.; Xu,
G.-Y.; Xuan, J. Radical Addition/Cyclization Reaction of 2-
Vinylanilines with Alkynes: Synthesis of Naphthalenes via
Electron Catalysis. Chem. Asian J., 2018, 13, 3855.
(15) Ravindran, B.; Sakthivel, K.; Suresh, C. G.; Pathak, T.
Diastereoselective Addition of Amines to Vinyl Sulfone
Modified Carbohydrates: A Highly Flexible Methodology for
the Synthesis of New Classes of Deoxyaminosugars. J. Org.
Chem. 2000, 65, 2637-2641.
(16) Reddick, J. J.; Cheng, J.; Roush, W. R. Relative Rates of
Michael Reactions of 2 ‘-(Phenethyl) Thiol with Vinyl
Sulfones, Vinyl Sulfonate Esters, and Vinyl Sulfonamides
Relevant to Vinyl Sulfonyl Cysteine Protease Inhibitors. Org.
Lett. 2003, 5, 1967.
(17) Wnuk, S. F.; Garcia, P. I.; Wang, Z. Radical-Mediated
Silyl-and Germyldesulfonylation of Vinyl and (α-Fluoro)
Vinyl Sulfones: Application of Tris(trimethylsilyl) Silanes and
Tris(trimethylsilyl) Germanes in Pd-Catalyzed Couplings. Org.
Lett. 2004, 6, 2047.
(18) (a) Arceo, E.; Jurberg, I. D.; Álvarez-Fernández, A.;
Melchiorre, P. Photochemical Activity of A Key Donor–
Acceptor Complex Can Drive Stereoselective Catalytic α-
Alkylation of Aldehydes. Nat. Chem. 2013, 5, 750. (b) Davies,
J.; Booth, S. G.; Essafi, S.; Dryfe, R. A. W.; Leonori, D.
Visible-Light-Mediated Generation of Nitrogen-Centered
Radicals: Metal-Free Hydroimination and Iminohydroxylation
Cyclization Reactions. Angew. Chem. Int. Ed. 2015, 54, 14017.
(c) Liu, B.; Lim, C.-H.; Miyake, G. M. Visible-Light-Promoted
C–S Cross-Coupling via Intermolecular Charge Transfer. J.
Am. Chem. Soc. 2017, 139, 13616. (d) Zhang, J.; Li, Y.; Xu,
R.; Chen, Y. Donor–Acceptor Complex Enables Alkoxyl
Radical Generation for Metal-Free C(sp3)–C(sp3) Cleavage and
Allylation/Alkenylation. Angew. Chem. Int. Ed. 2017, 129,
12793. (e) Li, Y.; Miao, T.; Li, P.; Wang, L. Photo-Driven
Synthesis of C6-Polyfunctionalized Phenanthridines from
Three-Component Reactions of Isocyanides, Alkynes, and
Sulfinic Acids by Electron Donor–Acceptor Complex. Org.
Lett. 2018, 20, 1735.
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
Kamenova, M.; Gevorgyan, V.
A Mild Light-Induced
Cleavage of the S–O Bond of Aryl Sulfonate Esters Enables
Efficient Sulfonylation of Vinylarenes. Chem. Sci. 2018, 9,
7193.
(11) (a) Jiang, Q.; Xu, B.; Jia, J.; Zhao, A.; Zhao,Y.-R.; Li, Y.-
Y.; He, N.-N.; Guo, C.-C. Copper-Catalyzed Aerobic
Decarboxylative Sulfonylation of Cinnamic Acids with
Sodium Sulfinates: Stereospecific Synthesis of (E)-Alkenyl
Sulfones. J. Org. Chem. 2014, 79, 7372. (b) Guo, R.; Gui, Q.;
Wang D.; Tan,Z. Synthesis of Vinylsulfones Via Palladium-
Catalyzed Decarboxylative Coupling of Cinnamic Acids with
Aromatic Sulfinic Acid Sodium Salts. Catal. Lett. 2014, 144,
1377. (c) Xu, Y.; Tang, X.; Hu, W.; Wu W.; Jiang, H.
Transition-Metal-Free Synthesis of Vinyl Sulfones via Tandem
Cross-Decarboxylative/Coupling Reactions of Sodium
Sulfinates and Cinnamic Acids. Green Chem. 2014, 16, 3720.
(d) Gao, J.; Lai, J.; Yuan, G. Iodine-Mediated Synthesis of (E)-
Vinyl Sulfones from Sodium Sulfinates and Cinnamic Acids in
Aqueous Medium. RSC Adv. 2015, 5, 66723. (e) Katrun,P.;
Hlekhlai,S.; Meesin, J.; Pohmakotr, M.; Reutrakul, V.;
Jaipetch, T.; Soorukram, D.; Kuhakarn, C. PhI(OAc)2
Mediated Decarboxylative Sulfonylation of β-Aryl-α,β-
Unsaturated Carboxylic Acids: A Synthesis of (E)-Vinyl
Sulfones. Org. Biomol. Chem. 2015, 13, 4785.
(19) (a) Emery, K. J.; Tuttle T.; Murphy, J. A. Evidence of
Single Electron Transfer from the Enolate Anion of An N, N’-
Dialkyldiketopiperazine Additive in BHAS Coupling
Reactions. Org. Biomol. Chem. 2017, 15, 8810. (b) Cumine, F.;
Zhou, S.; Tuttle T.; Murphy, J. A.
A
Study of
Diketopiperazines as Electron-Donor Initiators in Transition
Metal-Free Haloarene–Arene Coupling. Org. Biomol. Chem.
2017, 15, 3324.
(20) Studer A.; Curran, D. P. The Electron is A Catalyst. Nat. Chem.
2014, 6, 765.
(21) Song, C. X.; Chen, P.; Tang, Y. Carboxylation of Styrenes
with CBr4 and DMSO via Cooperative Photoredox and Cobalt
Catalysis. RSC Adv. 2017, 7, 11233.
(22) Cramer, N.; Miaskiewicz, S.; Reed, J. H.; Donets, P. A.;
Oliveira, C. C. Chiral 1,3,2-Diazaphospholenes as Catalytic
Molecular Hydrides for Enantioselective Conjugate Reductions.
Angew. Chem. Int. Ed. 2018, 57, 4039-4042.
(23) Gao, J.; Pan, X. J.; Liu, J.; Lai, J. Y.; Chang, L. M.; Yuan,
G. Q. Iodine-Induced Synthesis of Sulfonate Esters from
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