Sodium Dithionite-Mediated Decarboxylative Sulfonylation: Facile Access to Tertiary Sulfones

Article abstract of DOI:10.1002/anie.202001589

A straightforward multicomponent decarboxylative cross coupling of redox-active esters (N-hydroxyphthalimide ester), sodium dithionite, and electrophiles was established to construct sterically bulky sulfones. The inorganic salt sodium dithionite not only served as the sulfur dioxide source, but also acted as an efficient radical initiator for the decarboxylation. Notably, diverse naturally abundant carboxylic acids and artificially prepared carboxyl-containing drugs with multiple heteroatoms and sensitive functional groups successfully underwent this decarboxylative sulfonylation to provide sterically bulky tertiary sulfones. Mechanistic studies further demonstrated that decarboxylation was the rate-determining step and occurred via a single-electron transfer (SET) process with the assistance of sodium dithionite.

Full text of DOI:10.1002/anie.202001589

A Journal of the Gesellschaft Deutscher Chemiker
Angewandte
Chemie
International Edition
www.angewandte.org
Accepted Article
Title: Sodium Dithionite-Mediated Decarboxylative Sulfonylation: Facile
Access to Tertiary Sulfones
Authors: Yaping Li, Shihao Chen, Ming Wang, and Xuefeng Jiang
This manuscript has been accepted after peer review and appears as an
Accepted Article online prior to editing, proofing, and formal publication
of the final Version of Record (VoR). This work is currently citable by
using the Digital Object Identifier (DOI) given below. The VoR will be
published online in Early View as soon as possible and may be different
to this Accepted Article as a result of editing. Readers should obtain
the VoR from the journal website shown below when it is published
to ensure accuracy of information. The authors are responsible for the
content of this Accepted Article.
To be cited as: Angew. Chem. Int. Ed. 10.1002/anie.202001589
Angew. Chem. 10.1002/ange.202001589
Link to VoR: http://dx.doi.org/10.1002/anie.202001589
http://dx.doi.org/10.1002/ange.202001589

10.1002/anie.202001589
Angewandte Chemie International Edition
COMMUNICATION
Sodium Dithionite-Mediated Decarboxylative Sulfonylation: Facile
Access to Tertiary Sulfones
Yaping Li, Shihao Chen, Ming Wang,* and Xuefeng Jiang*
Dedicated to the 70th anniversary of Shanghai Institute of Organic Chemistry
Abstract: A straightforward multicomponent decarboxylative cross
coupling of redox-active esters (N-hydroxyphthalimide ester), sodium
dithionite and electrophiles was established to construct sterically
bulky sulfones. The inorganic salt sodium dithionite not only served
as the sulfur dioxide source, but also acted as an efficient radical
initiator for the decarboxylation. Notably, diverse naturally abundant
carboxylic acids and artificially prepared carboxyl-containing drugs
with multiple heteroatoms and sensitive functional groups
sucessfully underwent this decarboxylative sulfonylation to provide
sterically bulky tertiary sulfones. Mechanistic studies further
demonstrated that decarboxylation was the rate-determining step
and occurred via a single-electron transfer (SET) process with the
assistance of sodium dithionite.
Sulfones, as one of the top five most frequently applied drug
scaffolds,[1] have attracted considerable interest due to their
extensive applications in drug discovery.[2] Tertiary sulfones are
among the most important motifs in pharmaceuticals due to their
excellent effects on the rate of drug metabolism. A selection of
well-known tertiary sulfones as inhibitors is shown in Scheme
1A.[3-7] In addition, a sulfone, as a bioisostere of the carboxylic
motif, can be exchanged for
a
carboxyl group in
a
straightforward manner, which is of great significance for drug
discovery. Since DABSO [DABCO·(SO2)2] was first applied as a
sulfur dioxide surrogate,[8] strategies for the direct insertion of
SO2 into two coupling partners has been intensively studied due
to the step economy and oxidative economy of such strategies
for sulfone synthesis.[9] For example, transition-metal-catalyzed
syntheses of sulfones and sulfonamides via organometallic
reagents, which include boronic acids, organolithium reagents,
Grignard reagents and organosilanes, have been well
developed.[10]
Aryl/alkyl
halides[11]
and
aryldiazonium
Scheme 1. The construction of functional sulfones.
derivatives[12] can also be used as coupling partners for the
synthesis of primary and secondary sulfones (Scheme 1B). For
example, Wu et al developed the synthesis of sulfones from
(hetero)aryl iodides under catalyst-free conditions.[11d] However,
the introduction of sulfur dioxide adjacent to tertiary carbon
position of organic frameworks has not been reported owing to
the high steric hindrance in such processes. Recently, the Baran,
Oestreich, and Ohmiya et al groups demonstrated that redox-
active esters are prone to accepting an electron from transition
metal complexes or Breslow intermediates through a single-
electron transfer process.[13] According to our concept of
masked inorganic sulfur salts,[14] masks using sodium dithionite
(Na2S2O4) are excellent candidates of single-electron reductants
with unique free radical features. We envisioned that reductive
inorganic salt sodium dithionite can donate one electron to
redox-active. esters, resulting in the extrusion of CO2 and
generating a highly sterically hindered carbon radical; the other
half of the SO2 radical is then captured to construct the tertiary
sulfone (Scheme 1C). Based on our understanding of
organosulfur chemistry,[15] we disclose an efficient sodium
dithionite-mediated multicomponent decarboxylative coupling of
electrophiles, sodium dithionite and carboxylate-derived redox-
active esters to afford tertiary sulfones.
[*]
Y. Li, S. Chen, Dr. M. Wang, Prof. Dr. X. Jiang
Shanghai Key Laboratory of Green Chemistry and Chemical
Process, School of Chemistry and Molecular Engineering, East
China Normal University, 3663 North Zhongshan Road, Shanghai
200062, P. R. China
E-mail: xfjiang@chem.ecnu.edu.cn; wangming@chem.ecnu.edu.cn
Prof. Dr. X. Jiang
State Key Laboratory of Elemento-organic Chemistry, Nankai
University, Tianjin 300071, P. R. China
State Key Laboratory of Organometallic Chemistry, Shanghai
Institute of Organic Chemistry, Chinese Academy of Sciences, 345
Lingling Road, Shanghai 200032, P. R. China
Supporting information for this article is given via a link at the end of
the document.((Please delete this text if not appropriate))
This article is protected by copyright. All rights reserved.

10.1002/anie.202001589
Angewandte Chemie International Edition
COMMUNICATION
Table 1. Conditions optimization.[a]
We commenced the multicomponent decarboxylative cross
coupling with tertiary redox-active carboxylic ester 1a, sodium
dithionite and n-butyl bromide (2a). To increase the solubility of
inorganic salts,
a stoichiometric amount of phase transfer
reagent tetrabuylammonium bromide (TBAB) was added.
Delightedly, desired product 3a was prepared in 32% yield
without a base or an additive in the transformation (Table 1,
entry 1). A slight improvement was achieved by optimizing the
amount of water added, because it solubilized the salts (Table 1,
entry 2). A base is necessary to capture superfluous SO2
releasing from inorganic salt in the current transformation.
Various bases were further tested for their abilities to activate
the masking group of the inorganic sulfur salts, and DIPEA was
found to provide the best results (55% yield, Table 1, entries 3-
8). The addition of zinc chloride was found to facilitate product
formation (60% yield) since it favors decarboxylation via
chelation with the carbonyls (Table 1, entries 9-11). A mixed
solvent of N,N-dimethylformamide and acetonitrile was found to
be the best solvent, as it best solubilized the inorganic salt
(Table 1, entries 12-16). The efficiency of the transformation was
slightly lower in the absence of zinc chloride (Table 1, entry 17).
The multicomponent decarboxylative cross coupling reaction,
which allows the synthesis of functionalized tertiary sulfones, is
shown in Scheme 2. When alkyl bromides were used as the
electrophiles, a broad range of tertiary carboxylic acid-derived
esters with aryl (3a-3e) and alkyl (3f-3i) substituents on the
quaternary carbons, including sterically hindered adamantane
entry
1[b]
2
base
--
additive
--
solvent
DMA
Yield(%)
32
--
--
DMA
40
3
tBuOK
K2CO3
KHCO3
Et3N
--
DMA
NP
41
4
--
DMA
5
--
DMA
50
6
--
DMA
53
7
DMEDA
DIPEA
DIPEA
DIPEA
DIPEA
DIPEA
DIPEA
DIPEA
DIPEA
DIPEA
DIPEA
--
DMA
10
8
--
DMA
55
9
ZnCl2
MgCl2
LiCl
ZnCl2
ZnCl2
ZnCl2
ZnCl2
ZnCl2
--
DMA
60
10
11
12
13
14
15
16
17
DMA
42
DMA
50
DMSO
52
CH3CN
DMF
61
67
DMF:CH3CN = 1:1
DMF:CH3CN = 2:1
DMF:CH3CN = 2:1
74
79(73[c]
)
72
[a] Conditions: 1a (0.2 mmol), Na2S2O4 (0.4 mmol), nBuBr (0.6 mmol), base
(0.4 mmol), additive (0.1 mmol), TBAB (0.3 mmol), solvent (2.0 mL), 60 L of
H2O, 120 °C, N2, 15 h. NMR yields. [b] In the absence of H2O. [c] Isolated
yields.
Scheme 2. Collective sulfone construction.[a] [a] Conditions: 1 (0.2 mmol), 2 (0.6 mmol), Na2S2O4 (0.4 mmol), DIPEA (0.4 mmol), ZnCl2 (0.1 mmol), TBAB (0.3
mmol), DMF/CH3CN = 2:1 (2 mL), 60 L H2O, 120 oC, 15 h, isolated yields.
This article is protected by copyright. All rights reserved.

10.1002/anie.202001589
Angewandte Chemie International Edition
COMMUNICATION
Scheme 3. Decarboxylative Coupling of Naturally Occurring Carboxylic Acids and Carboxyl-Containing Clinically Relevant Drugs.[a] [a] Conditions: 1 (0.2 mmol), 2
(0.6 mmol), Na2S2O4 (0.4 mmol), DIPEA (0.4 mmol), ZnCl2 (0.1 mmol), TBAB (0.3 mmol), DMF/CH3CN = 2:1 (2 mL), 60 L H2O, 120 oC, 15 h, isolated yields.
and tertiary butyl groups, were efficiently achieved in good to
excellent yields. A series of cyclic (3j-3l) and linear (3m-3n)
secondary carboxylic acid-derived esters with different electronic
properties were well tolerated in this reaction. Primary 2-
(naphthalen-2-yl)acetic acid esters can also afford the desired
decarboxylative sulfonylation product (3o). The decarboxylative
cross coupling of the anti-inflammatory drug ibuprofen could
convert it to the corresponding sulfone, providing a useful
pathway for new drug discovery (3p). In the scope of alkyl
halides, linear alkyl (3q-3u), carbazole (3v) and thiophene
derivatives (3w) can readily participate in the multicomponent
decarboxylative coupling. In addition, phenoxy (3x), terminal
alkyne (3y), terminal olefins (3z), and strained four-membered
ring-containing (3aa) alkyl halide derivatives, were all tolerant in
the current decarboxylative sulfonylation and provided the
desired products with high efficiency. This transformation is also
compatible with secondary alkyl halides (3ab). Furthermore, this
decarboxylative sulfonylation can be successfully applied to
isoxepac-derived (3ac) and natural terpene citronellol-derived
(3ad) alkyl bromides. Notably, this transformation is not limited
to alkyl halides, and other electrophiles were shown to be
entirely compatible and afford the corresponding tertiary sulfone
products. The decarboxylative sulfonylation can be conducted
using stable and readily available phosphate esters as
electrophiles (3ae-3aj). Moreover, this straightforward coupling
can use alkyl toluenesulfonates as electrophiles to access
tertiary sulfones (3ak-3al).
decarboxylative sulfonylations of the anti-inflammatory drug
naproxen, ibuprofen and the anti-hyperlipoproteinemia drug
gemfibrozil were readily achieved using the described
transformation (4a-4c), which offers a convenient protocol for
the discovery of sulfone-containing drugs. The natural product
abietic acid was well tolerated (4d) and provided the
corresponding product with high diastereoselectivity (dr = 13:1).
Amino acids and saccharides, such as L-tyrosine, fructose and
glucose derivatives, were also compatible and afforded the
corresponding tertiary sulfone derivatives in good yields (4e-4g).
Tertiary sulfone-containing cholesterol 4h and estrone 4i were
efficiently obtained in good yields from the corresponding alkyl
halide precursors, and the structure of 4i was confirmed via X-
ray diffraction analysis.[16]
To determine the mechanism of the multicomponent
decarboxylative
coupling
reaction,
first,
2,2,6,6-
tetramethylpiperidine-1-oxyl (TEMPO) was added to the reaction
under the standard conditions, and the transformation was
suppressed (Scheme 4a-1). Subsequently, a radical clock
experiment involving (bromomethyl)cyclopropane (5) and alkyl
halide 2a was conducted under the standard conditions
(Scheme 4a-2). Cyclopropane-opened product 6 was generated
in 30% yield, which indicated that an alkyl radical intermediate
was involved in this transformation. Kinetic studies
demonstrated that the decarboxylation step was the rate-
determining step, and the formation and reaction of the alkyl
radical with sodium dithionite are fast (see supporting
information for detail). Thus, the postulated reaction pathway is
depicted in Scheme 4b. Initially, homolytic cleavage of sodium
dithionite furnished two sulfur dioxide radical anions 7. The
complex of ZnCl2 and carboxylic-derived redox-active ester 1
was formed via a chelating process, and this complex was
triggered by a SET from sulfur dioxide radical anion 7 to
To further demonstrate the broad applicability of this
multicomponent decarboxylative cross coupling protocol, we
sought to test the scope of the carboxylic acid derivative using
both the diverse readily available naturally occurring compounds
and synthetic carboxyl-containing drugs containning multiple
heteroatoms and sensitive functional groups (Scheme 3). The
This article is protected by copyright. All rights reserved.

10.1002/anie.202001589
Angewandte Chemie International Edition
COMMUNICATION
generate intermediate 8. The fragmentation of intermediate 8 led
to the generation of sterically hindered carbon radical 9 and
sodium phthalimide salt (NaNPhth) through the extrusion of CO2
with the assistance of ZnCl2. The capture of the other sulfur
dioxide radical anion (7) by sterically hindered carbon radical 9
furnished sulfonyl anion 10 and sulfinate salts 10′ in equilibrium.
Finally, alkylation coupling with the “soft” partner of intermediate
10 afforded desired sulfone product 3.[10b, 10e]
Keywords: sulfone • sulfur dioxide • sodium dithionite •
decarboxylative • radical
[1]
[2]
J. Wang, T. Hou, J. Chem. Inf. Model. 2010, 50, 55-67.
a) E. A. Ilardi, E. Vitaku, J. T. Njardarson, J. Med. Chem. 2014, 57,
2832-2842; b) M. Feng, B. Tang, S. Liang, X. Jiang, Curr. Top. Med.
Chem. 2016, 16, 1200-1216; c) K. A. Scott, J. T. Njardarson, Top. Med.
Chem. 2018, 376, 5; d) “Sulfur Chemistry”: X. Jiang, Topics in Current
Chemistry, Springer, Berlin, 2018; e) N. Wang, P. Saidhareddy, X.
Jiang, Nat. Prod. Rep. 2019, 36, DOI: 10.1039/C8NP00093J.
W. Fischli, J. P. Clozel, V. Breu, S. Buchmann, S. Mathews, H. Stadler,
E. Vieira, W. Wostl, Hypertension 1994, 24, 163-169.
[3]
[4]
[5]
[6]
C, H. Kleinbloesem, C. Weber, E. Fahrner, M. Dellenbach, H. Welker, V.
Schroter, G. G. Belz, Clin. Pharmacol. Ther. 1993, 53, 585-592.
K. M. Foote, K. Blades, A. Cronin, S. Fillery, S. S. Guichard, L. Hassall,
et al. J. Med. Chem. 2013, 56, 2125-2138.
H. Eto, Y. Kaneko, S. Takeda, M. Tokizawa, S. Sato, K. Yoshida, S.
Namiki, M. Ogawa, K. Maebashi, K. Ishida, M. Matsumoto, T. Asaoka,
Chem. Pharm. Bull. 2001, 49, 173-182.
[7]
[8]
P. H. Nicholls, R. H. Bromilow, T. M. Addiscott, Pestic. Sci. 1982, 13,
475-483.
a) P. S. Santos and M. T. S. Mello, J. Mol. Struct. 1988, 178, 121-133; b)
B. Nguyen, E. J. Emmet and M. C. Willis, J. Am. Chem. Soc. 2010, 132,
16372-16373; c) S. Ye and J. Wu, Chem. Commun. 2012, 48, 7753-
7755.
[9]
For books and reviews, see: a) J. Aziz, S. Messaoudi, M. Alami, A.
Hamze, Org. Biomol. Chem. 2014, 12, 9743-9759; b) E. J. Emmett, M.
C. Willis, Asian J. Org. Chem. 2015, 4, 602-611; c) Alex. S. Deeming, M.
C. Willis, 1,4-Disulfino-1,4-diazabicyclo [2.2.2]octane, bis(inner salt),
eEROS, Encyclopedia of Reagents for Organic Synthesis, Wiley, 2016;
d) G. Qiu, K. Zhou, L. Gao, J. Wu, Org. Chem. Front. 2018, 5, 691-705;
e) K. Hofman, N.-W. Liu, G. Manolikakes, Chem. -Eur. J. 2018,
24,11852-11863; f) G. Qiu, K. Zhou, J. Wu, Chem. Commun. 2018, 54,
12561-12569; g) S. Ye, G. Qiu, J. Wu, Chem. Commun. 2019, 55,
1013-1019.
Scheme 4. Mechanistic study.
In summary, a straightforward decarboxylative cross coupling
of carboxylate-derived redox-active esters, sodium dithionite and
electrophiles was developed to construct sterically congested
tertiary sulfones. Inorganic sodium dithionite served as not only
a sulfur dioxide source but also a radical initiator of the
decarboxylation via a SET process. Notably, various naturally
abundant carboxylic acids and synthetically prepared carboxyl-
[10] a) E. J. Emmett, B. R. Hayter, M. C. Willis, Angew. Chem. Int. Ed. 2013,
52, 12679-12683; Angew. Chem. 2013, 125, 12911-12915; b) M. W.
Johnson, S. W. Bagley, N. P. Mankad, R. G. Bergman, V. Mascitti, F.
D. Toste, Angew. Chem. Int. Ed. 2014, 53, 4404-4407; Angew. Chem.
2014, 126, 4493-4496; c) A. S. Deeming, C. J. Russell, M. C. Willis,
Angew. Chem. Int. Ed. 2015, 54, 1168-1171; Angew. Chem. 2015, 127,
1184-1187; d) A. Shavnya, K. D. Hesp, V. Mascitti, A. C. Smith, Angew.
Chem. Int. Ed. 2015, 54, 13571-13575; Angew. Chem. 2015, 127,
13775-13779; e) A. S. Deeming, C. J. Russell, M. C. Willis, Angew.
Chem. Int. Ed. 2016, 55, 747-750; Angew. Chem. 2016, 128, 757-760; f)
D. Zheng, R. Mao, Z. Li, J. Wu, Org. Chem. Front. 2016, 3, 359-363 ; g)
H. Zhu, Y. Shen, Q. Deng, J. Chen, T. Tu, ACS Catal. 2017, 7, 4655-
4659; h) Y. Chen, P. R. D. Murray, A. T. Davies, M. C. Willis, J. Am.
Chem. Soc. 2018, 140, 8781-8787.
containing drugs
underwent
efficient
decarboxylative
sulfonylation for the construction of diversely functionalized
tertiary sulfones. Mechanistic studies further demonstrated that
the alkyl radical and sulfur dioxide radical anion were involved
as intermediates, and the decarboxylation of the carboxylate-
derived redox-active ester was the rate-determining step in this
transformation. Further drug discovery studies with this SO2-
insertion coupling protocol are in progress in our laboratory.
[11] a) A. Shavnya, S. B. Coffey, A. C. Smith, V. Mascitti, Org. Lett. 2013, 15,
6226-6229; b) E. J. Emmett, B. R. Hayter, M. C. Willis, Angew. Chem.
Int. Ed. 2014, 53, 10204-10208; Angew. Chem. 2014, 126, 10368-
10372; c) J. Zhang, K. Zhou, G. Qiu, J. Wu, Org. Chem. Front. 2019, 6.
36-40; d) Y. Li, T. Liu, G. Qiu, J. Wu, Adv. Synth. Catal. 2019, 361,
1154-1159.
Acknowledgements
[12]
a) D. Zheng, J. Yu, J. Wu, Angew. Chem. Int. Ed. 2016, 55, 11925-
11929; Angew. Chem. 2016, 128, 12104-12108; b) F. Liu, J.-Y. Wang,
P. Zhou, G. Li, W.-J. Hao, S.-J. Tu, B. Jiang, Angew. Chem. Int. Ed.
2017, 56, 15570-15574; Angew. Chem. 2017, 129, 15776-15780; c) H.
Xia, Y. An, X. Zeng, J. Wu, Chem. Commun. 2017, 53, 12548-12551. d)
K. Zhou, J. Zhang, L. Lai, J. Cheng, J. Sun, J. Wu, Chem. Commun.
2018, 54, 7459-7462.
The authors are grateful for the financial support provided by
The National Key Research and Development Program of China
(2017YFD0200500), NSFC (21971065, 21722202, 21672069
and 21871089 for M.W.), S&TCSM of Shanghai (Grant
18JC1415600), Professor of Special Appointment (Eastern
Scholar) at Shanghai Institutions of Higher Learning, the
National Program for Support of Top-notch Young Professionals,
and Innovative Research Team of High-Level Local Universities
in Shanghai.
[13]
The C-C coupling of redox-active esters, see: a) J. Cornella, J. T.
Edwards, T. Qin, S. Kawamura, J. Wang, C.-M. Pan, R. Gianatassio, M.
Schmidt, M. D. Eastgate, P. S. Baran, J. Am. Chem. Soc. 2016, 138,
This article is protected by copyright. All rights reserved.

10.1002/anie.202001589
Angewandte Chemie International Edition
COMMUNICATION
2174-2177; b) T. Qin, J. Cornella, C. Li, L. R. Malins, J. T. Edwards, S.
Kawamura, B. D. Maxwell, M. D. Eastgate, P. S. Baran, Science 2016,
352, 801-805; c) F. Toriyama, J. Cornella, L. Wimmer, T.-G. Chen, D. D.
Dixon, G. Creech, P. S. Baran, J. Am. Chem. Soc. 2016, 138, 11132-
11135; d) W. Xue, M. Oestreich, Angew. Chem. Int. Ed. 2017, 56,
11649-11652; Angew. Chem. 2017, 129, 11808-11811; e) X.-G. Liu, C.-
J. Zhou, E. Lin, X.-L. Han, S.-S. Zhang, Q. Li, H. Wang, Angew. Chem.
Int. Ed. 2018, 57, 13096-13100; Angew. Chem. 2018, 130, 13280-
13284; f) T. Ishii, Y. Kakeno, K. Nagao, H. Ohmiya, J. Am. Chem. Soc.
2019, 141, 3854-3858; g) T. Ishii, K. Ota, K. Nagao, H. Ohmiya, J. Am.
Chem. Soc. 2019, 141, 14073-14077.
Wang, X. Jiang, Green Chem. 2020, 22‚ 322-326; c) M. Wang, J. Zhao,
X. Jiang, ChemSusChem 2019, 12, 3064-3068; d) M. Wang, Q. Fan, X.
Jiang, Green Chem. 2018, 20‚ 5469-5473; e) M. Wang, S. Chen, X.
Jiang, Org. Lett. 2017, 19‚ 4916-4919.
[15] a) M. Wang, Z. Dai, X. Jiang, Nat. Commun. 2019, 10, 2661; b) Y. Li, S.
A. Rizvi, D. Hu, D. Sun, A. Gao, Y. Zhou, J. Li, X. Jiang, Angew. Chem.
Int. Ed. 2019, 58, 13499-13509; Angew. Chem. 2019, 131, 13633-
13640; c) X. Xiao, J. Xue, X. Jiang, Nat. Commun. 2018, 9, 2191; d) Y.
Li, M. Wang, X. Jiang, ACS Catal. 2017, 7, 7587-7592; e) X. Xiao, M.
Feng, X. Jiang, Angew. Chem. Int. Ed. 2016, 55, 14121-14125; Angew.
Chem. 2016, 128, 14327-14331.
[14] a) Y. Meng, M. Wang, X. Jiang, Angew. Chem. Int. Ed. 2020, 59, 1346-
1353; Angew. Chem. 2020, 132, 1362-1369; b) S. Chen, Y. Li, M.
[16] CCDC 1974725 (4i) can be obtained free of charge from The Cambridge
Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
This article is protected by copyright. All rights reserved.

10.1002/anie.202001589
Angewandte Chemie International Edition
COMMUNICATION
Entry for the Table of Contents (Please choose one layout)
Layout 1:
COMMUNICATION
Yaping Li, Shihao Chen, Ming
Wang*, XuefengJiang*
Page No. – Page No.
Sodium Dithionite-Mediated
Decarboxylative Sulfonylation:
Facile Access to Tertiary Sulfones
A straightforward multicomponent decarboxylative cross coupling of redox-
active esters, sodium dithionite and electrophiles was established to construct
sterically bulky sulfones. The inorganic salt sodium dithionite not only served as
the sulfur dioxide source, but also acted as an efficient radical initiator for the
decarboxylation.
This article is protected by copyright. All rights reserved.