2015
DOI: 10.1021/acs.orglett.5b00529
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Iridium-Catalyzed ortho-Selective C–H Silylation of Aromatic Compounds Directed toward the Synthesis of π-Conjugated Molecules with Lewis Acid–Base Interaction

Abstract: We successfully developed an iridium-catalyzed ortho-selective C-H silylation of aromatic compounds. The reaction exhibited a wide substrate scope, and a variety of π-conjugated molecules were synthesized in good to excellent yields, even in gram scale. Several silyl groups could also be introduced into the products. The experimental results indicated that the regioselectivity could be controlled by a Lewis acid-base interaction between the Lewis acidic silicon atoms of fluorinated hydrosilanes and the Lewis b… Show more

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Cited by 38 publications
(19 citation statements)
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“…Therefore, 2-aryl pyridines (3) reacted with the hydrosilyl reagent (153) in the presence of Ir-catalyst under mild conditions to afford the desired product (154) in good yields (Scheme 79). [86] The presented experimental results suggesting that the regioselectivity could be controlled by Lewis acid À base interaction between the Lewis acidic fluorinated silicon atom of hydrosilane and the Lewis basic nitrogen atom of 2-aryl pyridines.…”
Section: Silylation Of 2-aryl Pyridinesmentioning
confidence: 89%
“…Therefore, 2-aryl pyridines (3) reacted with the hydrosilyl reagent (153) in the presence of Ir-catalyst under mild conditions to afford the desired product (154) in good yields (Scheme 79). [86] The presented experimental results suggesting that the regioselectivity could be controlled by Lewis acid À base interaction between the Lewis acidic fluorinated silicon atom of hydrosilane and the Lewis basic nitrogen atom of 2-aryl pyridines.…”
Section: Silylation Of 2-aryl Pyridinesmentioning
confidence: 89%
“…Acid Base Interaction between Two Substrates 3,4 In the case of the directing group assisted C H transformations discussed so far, the directing groups coordinate to a transition metal of the catalyst, and thus the metal center is brought close to a reaction site and subsequent C H activation and successive transformations occur ortho selectively (Scheme 1a). But C H borylation reactions usually occur at the meta and para positions of aromatic substrates, 5 and there had been no report on ortho selective C H borylation when we started to develop this reaction.…”
Section: Regioselective C H Transformations Controlled By Lewismentioning
confidence: 99%
“…As a result, the desired ortho selective C H silylation proceeded when an iridium catalyst was used, even on a gram scale (Scheme 3). 4 …”
Section: Regioselective C H Transformations Controlled By Lewismentioning
confidence: 99%
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“…Among the reported systems, intermolecular interactions investigated in molecular junctions include metal coordination bonds, 16 hydrogen bonds, [17][18][19] charge-transfer effects, 20 host-guest interactions 21 and π-π stacking. 22,23 In the investigation below, our interest in Lewis acid-base interactions stems from the fact that they are quite strong and prevalent in supramolecular coordination chemistry, 24 as well as in organic synthetic methodologies, such as controlling regioselectivity in silylation 25 and catalytic processes. [26][27][28] As a consequence, we set our course towards exploiting strong Lewis acid-base interactions to regulate the tunneling mechanism, and hence to affect the electron transport through molecular wires.…”
mentioning
confidence: 99%