Reaction of organoboranes with chloroacetonitrile under the influence of potassium 2,6-Di-tert-butylphenoxide. A convenient procedure for the conversion of olefins into nitriles via hydroboration

Brown, Herbert C.; Nambu, Hirohiko; Rogić, Milorad M.

doi:10.1021/ja01052a056

Cited by 48 publications

(6 citation statements)

References 2 publications

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“…Chloroacetonitrile thus became our preferred starting material in order to avoid C–H arylation at the first step and then rely on steric effects to prevent over-arylation in subsequent C–H functionalizations . For the Suzuki–Miyaura coupling of phenylboronic acid with chloroacetonitrile, we found that Pd(OAc) 2 and SPhos along with aqueous Na 2 CO 3 provided monoaryl acetonitriles 2 in good to excellent yields.…”

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confidence: 96%

The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation: A New Synthetic Approach to Tri- and Tetraarylmethanes

et al. 2014

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The selective synthesis of multiarylated acetonitriles via sequential palladium-catalyzed arylations of chloroacetonitrile is reported. The three aryl groups are installed via a Pd-catalyzed Suzuki-Miyaura cross coupling reaction followed by back-to-back C-H arylations to afford triarylacetonitriles in three steps with no over-arylation at any step. The triarylacetonitrile products can be converted into highly functionalized species including tetraarylmethanes. This new strategy provides rapid access to a variety of unsymmetrical tri- and tetraarylmethane derivatives from simple, readily available starting materials.

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confidence: 96%

The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation: A New Synthetic Approach to Tri- and Tetraarylmethanes

et al. 2014

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“…Thus, it was of interest to examine transformations that might apply to Ni‐catalyzed conjunctive coupling products. As depicted in Figure , while well‐established oxidation delivers alcohol 1 effectively, C−C bond‐forming cyanomethylation was also found to apply in a one pot protocol, directly with the 9‐BBN derivative, delivering 28 with excellent stereospecificity. In connection to other reactions, important studies by Aggarwal revealed a strong migratory aptitude of the 9‐BBN bicyclooctane ring that often outcompetes migration of other alkyl substituents.…”

Section: Methodsmentioning

confidence: 93%

Nickel‐Catalyzed Enantioselective Conjunctive Cross‐Coupling of 9‐BBN Borates

2017

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“…Second, the enhanced electrophilicity of trialkylboranes relative to boronic esters allows the former to engage in reactions that are unavailable to the latter. Especially powerful reactions that apply to 9-BBN derivatives include an inexpensive CO-based homologation [2] , homologations with α-haloacetate derivatives [3] , and O'Donnell catalytic asymmetric amino acid syntheses. [4] Despite this synthesis utility, there is a lack of methods available for the asymmetric synthesis of 9-BBN derivatives.…”

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confidence: 99%

“…Thus, it was of interest to examine transformations that might apply to Ni-catalyzed conjunctive coupling products. As depicted in Figure 2, while well-established oxidation [15] delivers alcohol 1 effectively, C-C bond-forming cyanomethylation [3c] was also found to apply in a one pot protocol, directly with the 9-BBN derivative, delivering 28 with excellent stereospecificity. In connection to other reactions, important studies by Aggarwal [14a] revealed a strong migratory aptitude of the 9-BBN bicyclooctane ring that often outcompetes migration of other alkyl substituents.…”

mentioning

confidence: 99%