Abstract
Phosphonium and benzotriazolyloxy (and related) intermediates
are easily prepared by the reactions of cyclic amides and ureas
with (1H -benzotriazol-1-yloxy)triaminophosphonium hexafluorophosphate
related reagents. The former intermediates could also be made available
using analogous phosphonium reagents prepared in situ or from commercial
sources. These intermediates efficiently lead to carbon-nitrogen,
carbon-oxygen, carbon-sulfur, and carbon-carbon
bond formations through nucleophilic aromatic substitution reactions
with various nucleophiles. A new reaction involving the
generation of phenols in situ from arylboronic acids and oxygen
under palladium(0) catalysis or with boronic acids and hydrogen
peroxide is reviewed.
1 Introduction
2 Phosphonium-Mediated Nucleophilic Aromatic Substitution Reactions
of Heterocyclic Systems
2.1 Phosphonium-Mediated Carbon-Nitrogen Bond Forming Reactions
via Modified Appel Conditions
2.2 Phosphonium-Mediated Carbon-Nitrogen Bond Forming Reactions
via Commercially Available Phosphonium Reagents
2.2.1 (1H -Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium
Hexafluorophosphate as an Activating Agent
2.2.2 (1H -Benzotriazol-1-yloxy)tripyrrolidinylphosphonium Hexafluorophosphate
and Bromotripyrrolidinylphosphonium Hexafluorophosphate as Activating
Agents
2.2.3 Solvent and Base Effects
2.3 Reactivity of Various Phosphonium Reagents
2.4 Phosphonium-Mediated Carbon-Oxygen, Carbon-Sulfur, and
Carbon-Carbon Bond Forming Reactions
3 Benzotriazolyloxy-Mediated and Related Bond-Forming Reactions
of Heterocyclic Systems
4 Phosphonium-Mediated Reaction Mechanisms
4.1 Stepwise Pathways via Phosphonium and 1H -Benzotriazol-1-ol
(or Pyridotriazol-1-ol) Adducts
4.2 1H -Benzotriazol-1-ol (or Pyridotriazol-1-ol)
Adduct Independent Pathway
5 Palladium-Catalyzed Heteroaryl Ether Formation from Benzotriazolyloxy-
or Pyridotriazolyloxy-Substituted Heterocycles with Arylboronic
Acids
6 Unusual 1H -Benzotriazol-1-ol Adduct
Rearrangement
7 A Tentative Protection and Amination Strategy Involving a 1H -Benzotriazol-1-ol Adduct
8 Conclusion and Outlook
Key words
phosphonium - benzotriazoles - nucleophilic
aromatic substitutions - aryl ethers - aminations
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(TTPT) has not been reported to the best of our knowledge. Because
of the close structural relationship of these compounds, experienced medicinal
chemists could easily assume similar toxic effects until TTPT is
tested or clear SARs have been established. Therefore, the same
precautions should be taken when handling these compounds! One of
the shared health concerns is that both liquid chemicals might cause respiratory
problems, despite the fact that both liquids have relatively high
boiling points (HMPA: 230-232 ˚C at 740 mmHg;
TTPT: 140-142 ˚C at 0.1 mmHg) and reasonable flash
points (HMPA: 144 ˚C, closed cup; TTPT: 112.8 ˚C, closed
cup. See Aldrich material safety data sheets for HMPA (product number
52730) and TTPT (product number 93404).
