Redox-neutral organocatalytic Mitsunobu reactions
Keyword(s):
Nucleophilic substitution reactions of alcohols are among the most fundamental and strategically important transformations in organic chemistry. For over half a century, these reactions have been achieved by using stoichiometric, and often hazardous, reagents to activate the otherwise unreactive alcohols. Here, we demonstrate that a specially designed phosphine oxide promotes nucleophilic substitution reactions of primary and secondary alcohols in a redox-neutral catalysis manifold that produces water as the sole by-product. The scope of the catalytic coupling process encompasses a range of acidic pronucleophiles that allow stereospecific construction of carbon-oxygen and carbon-nitrogen bonds.
1975 ◽
Vol 40
(14)
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pp. 2037-2042
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2006 ◽
Vol 36
(11)
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pp. 1479-1484
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1995 ◽
Vol 60
(20)
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pp. 6592-6594
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1974 ◽
Vol 96
(10)
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pp. 3255-3261
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