2019
DOI: 10.1002/anie.201812806
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Reductive Molybdenum‐Catalyzed Direct Amination of Boronic Acids with Nitro Compounds

Abstract: The synthesis of aromatic amines is of utmost importance in aw ide range of chemical contexts.W er eport ad irect amination of boronic acids with nitro compounds to yield (hetero)aryl amines.T he novel combination of ad ioxomolybdenum(VI) catalyst and triphenylphosphine as inexpensive reductant has revealed to be decisive to achieve this new CÀNc oupling. Our methodology has proven to be scalable,a ir and moisture tolerant, highly chemoselective and engages both aliphatic and aromatic nitro compounds.M oreover… Show more

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Cited by 107 publications
(79 citation statements)
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“…The successful transformation of aliphatic nitro compounds in our three‐component reaction precludes this reaction course since aliphatic nitroso compounds would rapidly tautomerize to oximes. Similar observations have been made by other authors …”
Section: Methodssupporting
confidence: 93%
See 3 more Smart Citations
“…The successful transformation of aliphatic nitro compounds in our three‐component reaction precludes this reaction course since aliphatic nitroso compounds would rapidly tautomerize to oximes. Similar observations have been made by other authors …”
Section: Methodssupporting
confidence: 93%
“…This property has been exploited to make them react with various nitrenoid species that can be generated in situ by the reduction of nitro compounds in the presence of phosphetanes and phosphines . Both aliphatic and aromatic nitro compounds have been transformed into secondary anilines by using both an excess of boronic acid and of PPh 3 in combination with a molybdenum catalyst …”
Section: Methodsmentioning
confidence: 99%
See 2 more Smart Citations
“…Thus, clearly, practical step and redox efficient strategies to build the indole scaffold are still in high demand, in particular using non-ortho functionalized nitroarenes. Herein, we propose to develop such a strategy, by directly intercepting the reduction of the nitroarene substrate [29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45][46] to achieve a straightforward Rh-catalysed C-H bond activation [47][48][49][50][51][52] event and coupling with the alkyne. We thus started with nitrobenzene and diphenylacetylene as model substrates, in the presence of catalytic amounts of the classical [Cp*RhCl 2 ] 2 dimer.…”
mentioning
confidence: 99%