Abstract
The utility of the 2-pyridylsilyl group as a multifunctional group in organic synthesis
is described. The use of the 2-pyridylsilyl group as a removable directing group is
a powerful synthetic strategy that circumvents the specificity-generality dilemma
in metal-mediated organic synthesis. In addition, the utility of the 2-pyridylsilyl
group as a phase tag for strategic separation and as a removable hydrophilic group
for aqueous reactions is also described.
1 Introduction
2 Transformations of the 2-Pyridylsilyl Group to Other Groups
3 The 2-Pyridylsilyl Group as a Removable Directing Group for Organometallic Reactions
3.1 Deprotonative Lithiation of Methyl(2-pyridyl)silanes
3.2 Peterson Olefination Using [Bis(2-pyridylsilyl)methyl]lithium
3.3 Carbomagnesation Across Alkenyl(2-pyridyl)silanes
3.4 Carbomagnesation Across Alkynyl(2-pyridyl)silanes
3.5 Mizoroki-Heck Reaction of Alkenyl(2-pyridyl)silanes
3.6 Hiyama Coupling of Alkenyl(2-pyridyl)silanes
3.7 Homocoupling of Alkenyl(2-pyridyl)silanes
3.8 Programmable Synthesis of Arylethene-Based Extended
3.9 Pauson-Khand Reaction Using Alkenyl(2-pyridyl)silanes
3.10 Stille Coupling of Stannylmethyl(2-pyridyl)silanes
3.11 Hiyama Coupling of Benzyl(2-pyridyl)silanes
3.12 Carbonyl Allylation Using Allyl(2-pyridyl)silanes
3.13 Hydrosilylation Using Hydro(2-pyridyl)silanes
3.14 Allylic Alkylation Directed by the 2-Pyridylsilyl Group
4 The 2-Pyridylsilyl Group as a Phase Tag for Solution-Phase Synthesis
5 The 2-Pyridylsilyl Group as a Removable Hydrophilic Group for Aqueous Reactions
5.1 Diels-Alder Reaction
5.2 Photocycloaddition
6 Conclusions and Outlook
Key words
2-pyridylsilyl group - removable directing group - phase tag
References and Notes
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Catalog numbers in Tokyo Kasei Kogyo Co., Ltd (TCI): 1 (T 2021), 9 (M 1460), 15 (D 2935), 58 (D 2934).
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Over 500 compounds (>200 pyridylsilylated and >300 non-pyridylsilylated compounds)
were synthesized using this chemistry.
