Chemoselective reduction of isothiocyanates to thioformamides mediated by the Schwartz reagent
Literature Information
Karen de la Vega-Hernández, Raffaele Senatore, Margherita Miele, Ernst Urban, Wolfgang Holzer, Vittorio Pace
Thioformamides are easily prepared – under full chemocontrol – through the partial reduction of isothiocyanates with the in situ generated Schwartz reagent. The high electrophilicity of the starting materials enables the straightforward addition of the hydride ion, thus constituting a reliable and high-yielding method for obtaining variously functionalized thioformamides. Sensitive chemical groups to the reduction conditions such as nitro, ester, alkene, azo, azide and keto groups do not interfere with the chemoselectivity of the process. Moreover, the stereochemical information embodied in the starting material is fully retained in the final products. The synthetic potential of the selected thioformamide template is also briefly discussed.
Recommended Journals
Related Literature
Direction control in DNA binding of chiral d-lysine-based peptide nucleic acid (PNA) probed by electrospray mass spectrometry
Stefano Sforza, Tullia Tedeschi, Roberto Corradini, Arnaldo Dossena, Rosangela Marchelli
DOI: 10.1039/B212718K
Highly enantioselective hydrolysis of alicyclic meso-epoxides with a bacterial epoxide hydrolase from Sphingomonas sp. HXN-200: simple syntheses of alicyclic vicinal trans-diols
Dongliang Chang, Zunsheng Wang, Maarten F. Heringa, Renato Wirthner, Bernard Witholt, Zhi Li
DOI: 10.1039/B300435J
A sequential highly stereoselective hydroboration and Suzuki–Miyaura cross-coupling reaction of fluoroalkylated internal acetylenes: a practical one-pot synthesis of fluoroalkylated trisubstituted alkenes
Tsutomu Konno, Jungha Chae, Tomoo Tanaka, Takashi Ishihara, Hiroki Yamanaka
DOI: 10.1039/B316065C
Silica coated fullerenols: seeded growth of silica spheres under acidic conditions
Elizabeth A. Whitsitt, Andrew R. Barron
DOI: 10.1039/B212808J
Ni(iii) vs. Ni(ii)-thiyl radical: charge-delocalisation in a binuclear Ni(iii)Ni(ii)-dithiolate complex
Neil D. J. Branscombe, Andrew J. Atkins, Armando Marin-Becerra, Eric J. L. McInnes, Frank E. Mabbs, Jonathan McMaster, Martin Schröder
DOI: 10.1039/B300245D
Selective growth of a less stable polymorph of 2-iodo-4-nitroaniline on a self-assembled monolayer template
Rupa Hiremath, Stephen W. Varney, Jennifer A. Swift
DOI: 10.1039/B411649F
A new route to fullerene substituted phenylalanine derivatives
Jianzhong Yang, Andrew R. Barron
DOI: 10.1039/B411118D
1,4-Dihydro-1,4-diphosphinine fused with two tetrathiafulvalenes
Narcis Avarvari, Marc Fourmigué
DOI: 10.1039/B412193G
Cyclopropyl fatty acids implicate a radical but not a cation as an intermediate in P450BM3-catalysed hydroxylations
Max J. Cryle, Julia M. U. Stuthe, Paul R. Ortiz de Montellano, James J. De Voss
DOI: 10.1039/B315911F
Self-assembled arrays of zinc oxide nanoparticles from monolayer films of diblock copolymer micelles
Seong Il Yoo, Byeong-Hyeok Sohn, Wang-Cheol Zin, Sung-Jin An, Gyu-Chul Yi
DOI: 10.1039/B409934F
You might also like
What industries use (1R,3S)-1,3-Cyclopentanediol (CAS: 16326-97-9)?
(1R,3S)-1,3-Cyclopentanediol finds applications in various industries. In the ph...
What precautions should be taken when handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine (CAS: 637-31-0)?
When handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine, it i...
Are there alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine (CAS: 1352318-16-1) in synthesis?
There are several alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine in ...
What regulatory guidelines apply to 1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6)?
1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6) must comply with the Globally...
Is Tetrodotoxin Citrate (CAS: 18660-81-6) safe?
Tetrodotoxin Citrate is extremely dangerous and should be handled with extreme c...
What are the main uses of 2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9)?
2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9) i...
How should waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) be handled?
Waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) ...
How is 2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl}carbamate (CAS: 102507-19-7) typically synthesized?
2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl...
What is Benzeneethanamine, α-ethyl-, hydrochloride (1:1) (CAS: 20735-15-3)?
Benzeneethanamine, α-ethyl-, hydrochloride (1:1) is an organic compound with the...
Are there alternatives to 3-{(E)-[4-(Dimethylamino)phenyl]diazenyl}benzoic acid (CAS: 20691-84-3) in synthesis?
In the synthesis of compounds similar to 3-{(E)-[4-(Dimethylamino)phenyl]diazeny...
Source Journal
Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.














