Categories: C-S Bond Formation >
Synthesis of sulfonamides
Related |
 |
 |
|
 |
 |
 |
 |
Recent Literature
Primary sulfonamides can be synthesized from organometallic reagents and a
novel sulfinylamine reagent, t-BuONSO in a convenient one-step process. A
variety of (hetero)aryl and alkyl Grignard and organolithium reagents perform
well in the reaction, providing primary sulfonamides in good to excellent yields.
T. Q. Davies, M. J. Tilby, D. Skolc, A. Hall, M. C. Willis, Org. Lett., 2020, 22, 9495-9499.
The bench-stable colorless solid charge-transfer complex generated from the
combination of DABCO and sulfur dioxide, DABSO, can replace gaseous sulfur
dioxide in organic synthesis. Reactions with Grignard reagents form sulfinates,
which can then be converted in situ to sulfonamides. Alternatively, reaction
with anilines and iodine leads to the formation of a series of sulfamides.
H. Woolven, C. Gonzáles-Rodríguez, I. Marco, A. L. Thompson, M. C. Willis, Org. Lett., 2011,
13, 4876-4878.
Readily available and structurally diverse alkyl carboxylic acids can serve as
the starting materials for sulfinamides, sulfonamides, and sulfonimidamides
syntheses. The methods harness alkyl radical generation from carboxylic acids
using acridine photocatalysts and 400 nm light with subsequent radical addition
to sulfinylamine reagents, delivering sulfinamide products.
J. A. Andrews, J. Kalepu, C. F. Palmer, D. L. Poole, K. E. Christensen, M. C.
Willis, J. Am. Chem. Soc.,
2023, 145, 21623-21629.
A simple copper-catalyzed aminosulfonylation of aryldiazonium tetrafluoroborates,
DABCO·(SO2)2, and N-chloroamines provides a
wide range of sulfonamides in good yields under mild conditions. Mechanistic
investigation suggests that a radical process and transition-metal catalysis
take place.
F. Zhang, D. Zheng, L. Lai, J. Cheng, J. Sun, J. Wu, Org. Lett.,
2018, 20, 1167-1170.
A Pd-catalyzed coupling of aryl iodides and the sulfur dioxide surrogate DABSO
provides aryl ammonium sulfinates, that can be transformed in a one-pot process
to various functionalized sulfonamides by simple treatment with an aqueous
solution of the relevant amine and sodium hypochlorite (bleach). A broad range
of amines, including anilines, and amino acid derivatives can be used.
E. F. Flegeau, J. M. Harrison, M. C. Willis,
Synlett, 2016, 27, 101-105.
A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic
acids, and potassium pyrosulfite provides a broad
range of sulfonamides bearing different reactive functional groups in very good yields through sequential C-S and S-N coupling.
K. Chen, W. Chen, B. Han, W. Chen, M. Liu, H. Wu,
Org. Lett., 2020, 22, 1841-1845.
Sulfamoyl chlorides can be easily activated by Cl-atom abstraction in the
presence of a silyl radical. This mode of activation can be used for a
single-step hydrosulfamoylation using inexpensive olefins,
tris(trimethylsilyl)silane, and photocatalyst Eosin Y.
S. M. Hell, C. F. Meyer, G. Laudadio, A. Misale, M. C. Willis, T. Noël, A. A.
Trabanco, V. Gouverneur, J. Am. Chem. Soc.,
2020, 142, 720-725.
A practical photoredox-catalyzed generation of sulfamyl radicals followed by
radical sulfonamidation of enol silyl ethers provides functionalized
β-ketosulfonamides in good yields under mild conditions.
Q. Luo, R. Mao, Y. Zhu, Y. Wang, J. Org. Chem., 2019, 84,
13897-13907.
Related
A mild, rapid, straightforward visible-light-mediated sulfonamide ethylation of
easily available redox active esters or alkyl iodides with vinylsulfonamides
provides a diverse array of compounds with C(sp3)-sulfonamide
skeletons. This method offers a broad substrate scope and has and
potential utility for late-stage functionalization of natural products and
synthetic medicines.
M. Zhang, M. Yu, Z. Wang, Y. Liu, Q. Wang, Org. Lett.,
2022, 24, 3932-3937.