PMID- 38477977
OWN - NLM
STAT- Publisher
LR  - 20240327
IS  - 1864-564X (Electronic)
IS  - 1864-5631 (Linking)
DP  - 2024 Mar 13
TI  - Preparation of Sulfonyl Chlorides by Oxidative Chlorination of Thiols and 
      Disulfides using HNO(3)/HCl/O(2) in a Flow Reactor.
PG  - e202400292
LID - 10.1002/cssc.202400292 [doi]
AB  - A continuous flow metal-free protocol for the synthesis of sulfonyl chlorides 
      from thiols and disulfides in the presence of nitric acid, hydrochloric acid and 
      oxygen was developed. The influence of the reaction parameters was investigated 
      under batch and flow conditions. Online (19)F NMR was successfully implemented to 
      investigate different reaction conditions within a single experiment. The 
      sulfonyl chlorides were isolated (mostly in 70-81 % yield) after performing a 
      simple aqueous washing procedure. In particular, the protocol was successfully 
      operated for >6 hours to convert diphenyl disulfide to its corresponding sulfonyl 
      chloride, achieving a throughput of 3.7 g h(-1). The environmental impact of the 
      protocol was assessed and compared to an existing continuous flow protocol using 
      1,3-dichloro-5,5-dimethylhydantoin (DCH) as reagent. The process mass intensity 
      (PMI) for the newly-developed flow protocol (15) compared favorably to the DCH 
      flow process (20).
CI  - (c) 2024 Wiley-VCH GmbH.
FAU - Sulzer, Niklas
AU  - Sulzer N
AD  - Center for Continuous Flow Synthesis and Processing (CCLOW), Research Center 
      Pharmaceutical Engineering GmbH (RCPE), Inffeldgasse 13, 8010, Graz, Austria.
AD  - Institute of Chemistry, University of Graz, Heinrichstrasse 28, 8010, Graz, 
      Austria.
FAU - Polterauer, Dominik
AU  - Polterauer D
AD  - Center for Continuous Flow Synthesis and Processing (CCLOW), Research Center 
      Pharmaceutical Engineering GmbH (RCPE), Inffeldgasse 13, 8010, Graz, Austria.
AD  - Institute of Chemistry, University of Graz, Heinrichstrasse 28, 8010, Graz, 
      Austria.
FAU - Hone, Christopher A
AU  - Hone CA
AUID- ORCID: 0000-0002-5939-920X
AD  - Center for Continuous Flow Synthesis and Processing (CCLOW), Research Center 
      Pharmaceutical Engineering GmbH (RCPE), Inffeldgasse 13, 8010, Graz, Austria.
AD  - Institute of Chemistry, University of Graz, Heinrichstrasse 28, 8010, Graz, 
      Austria.
FAU - Kappe, C Oliver
AU  - Kappe CO
AD  - Center for Continuous Flow Synthesis and Processing (CCLOW), Research Center 
      Pharmaceutical Engineering GmbH (RCPE), Inffeldgasse 13, 8010, Graz, Austria.
AD  - Institute of Chemistry, University of Graz, Heinrichstrasse 28, 8010, Graz, 
      Austria.
LA  - eng
GR  - Research Center Pharmaceutical Engineering (RCPE)/
GR  - COMET Competence Centers for Excellent Technologies/
PT  - Journal Article
DEP - 20240313
PL  - Germany
TA  - ChemSusChem
JT  - ChemSusChem
JID - 101319536
SB  - IM
OTO - NOTNLM
OT  - continuous flow
OT  - gas-liquid
OT  - oxidative chlorination
OT  - sulfonyl chloride
EDAT- 2024/03/13 12:43
MHDA- 2024/03/13 12:43
CRDT- 2024/03/13 11:54
PHST- 2024/03/07 00:00 [revised]
PHST- 2024/02/12 00:00 [received]
PHST- 2024/03/13 12:43 [pubmed]
PHST- 2024/03/13 12:43 [medline]
PHST- 2024/03/13 11:54 [entrez]
AID - 10.1002/cssc.202400292 [doi]
PST - aheadofprint
SO  - ChemSusChem. 2024 Mar 13:e202400292. doi: 10.1002/cssc.202400292.