Categories: C-S Bond Formation >
Synthesis of aryl sulfides and diaryl sulfides
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Recent Literature
A general palladium-catalyzed reaction using the CyPF-t-Bu ligand for
the coupling of aryl halides and sulfonates with thiols exhibits
extraordinary turnover numbers and high tolerance of functional groups.
M. A. Fernández-Rodríguez, Q. Shen, J. F. Hartwig, J. Am. Chem. Soc.,
2006, 128, 2180-2181.
A versatile and efficient Pd(OAc)2/1,1'-bis(diisopropylphosphino)ferrocene-catalyzed
cross-coupling of thiols with aryl halides was developed. Aryl bromides and
chlorides can be coupled to aliphatic and aromatic thiols - the widest substrate
scope of any reported to date. This catalyst system also enables the coupling of
secondary phosphines with aryl halides.
M. Murata, S. L. Buchwald, Tetrahedron, 2004, 60,
7397-7403.
Rongalite promotes a smoth, one-pot synthesis of aryl alkyl sulfides from
disulfides and alkyl halides at room temperature. This protocol is metal-free,
strong-base-free, and offers mild reaction conditions, operational simplicity,
short reaction times and high yields of products.
R.-y. Tang, P. Zhong, Q.-l. Lin, Synthesis, 2007, 85-91.
Unsymmetrical diorgano-monosulfides, selenides, and tellurides can be
synthesized by the coupling of dichalcogenides with aryl- or alkylboronic acids
using a copper catalyst in air. The present reaction takes advantage of both
organochalcogenide groups on the dichalcogenide.
N. Taniguchi, J. Org. Chem., 2007,
72, 1241-1245.
A cobalt-catalyzed coupling of aryl halides with thiophenols and
alkanethiols allows the preparation of various aryl sulfides in excellent yields
under mild reaction conditions.
Y.-C. Wong, T. T. Jayanth, C.-H. Cheng, Org. Lett., 2006, 8, 5613-5616.
Y.-C. Wong, T. T. Jayanth, C.-H. Cheng, Org. Lett., 2006, 8, 5613-5616.
1,1,1-Tris(hydroxymethyl)ethane as a New, Efficient, and Versatile Tripod
Ligand for Copper-Catalyzed Cross-Coupling Reactions of Aryl Iodides with
Amides, Thiols, and Phenols
Y.-J. Chen, H.-H. Chen, Org. Lett., 2006, 8, 5609-5612.
A mild, palladium-free method for C-S-bond formation is reported. The
standard protocol gave aryl sulfides in excellent yields from thiols and
iodides.
C. G. Bates, R. K. Gujadhur, D. Venkataraman, Org. Lett., 2002, 4, 2803-2806.
A nickel-catalyzed alkyl- or arylthiolation of aryl iodides with disulfides
allows the preparation of various aryl sulfides. The in situ generated
Ni(0)-bpy complex converts ArI into ArSR under neutral conditions.
Furthermore, this system enables the use of only 0.5 eq. (RS)2.
N. Taniguchi, J. Org. Chem., 2004, 69, 6904-6906.
A highly selective anti-Markovnikov addition of thiols to unactivated alkenes in
water at room temperature without any additive is a very simple and efficient
method for the synthesis of linear thioethers.
B. C. Ranu, T. Mandal, Synlett, 2007,
925-928.
A rapid conjugate addition of thiols to α,β-unsaturated ketones is achieved
in a hydrophobic ionic liquid [bmim]PF6/H2O solvent system in the absence of any acid catalyst. This mild and neutral method gave the
corresponding Michael adducts in high yields with excellent
1,4-selectivity. The ionic liquid can be reused.
J. S. Yadav, B. V. S. Reddy, G. Baishya, J. Org. Chem., 2003, 68, 7098-7100.
CeCl3 • 7H2O/NaI supported on
neutral alumina (Al2O3) promotes heteroatom Michael
additions under solvent-free conditions. The CeCl3 • 7H2O/NaI/Al2O3
system works well for hetero-Michael additions of weak nucleophiles such as
imidazoles and carbamates to various acceptors.
G. Bartoli, M. Bartolacci, A. Giuliani, E. Marcantoni, M. Massaccesi, E.
Torregiani, J. Org. Chem., 2005,
70, 169-174.
A mild, versatile, palladium-free method for the synthesis of vinyl sulfides
using the soluble copper(I) catalyst [Cu(phen)(PPh3)2]NO3
is reported. The desired vinyl sulfides are obtained with retention of
stereochemistry in good to excellent yields.
C. G. Bates, P. Saejueng, M. Q. Doherty, D. Venkataraman, Org. Lett., 2004, 6, 5005-5008.
An efficient, mild and transition-metal-free N-arylation of amines,
sulfonamides, and carbamates and O-arylation of phenols and carboxylic acids has
been achieved by using various o-silylaryl triflates in the presence of CsF.
Z. Liu, R. C. Larock, J. Org. Chem., 2006, 71, 3198-3209.
A regio and anti-selective copper-catalyzed 1,2-hydroxysulfenylation
of alkenes can be carried out by the use of disulfides and acetic acid.
Reoxidation of intermediate sulfides by oxygen enables the use of both
organosulfide groups of the disulfides.
N. Taniguchi, J. Org. Chem., 2006, 71, 7874-7876.
