Three-component reactions of CF3-substituted boranes, ethyl diazoacetate and imines

Elkin, Pavel K.; Levin, Vitalij V.; Dilman, Alexander D.; Стручкова, Марина И.; Arkhipov, Dmitry E.; Korlyukov, Alexander A.

doi:10.1016/j.tetlet.2012.08.153

Cited by 7 publications

(4 citation statements)

References 14 publications

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“…Borate 172 is an air-stable solid and storable in a tightly closed flask at room temperature for months without noticeable changes . The synthetic applications of 172 have been studied, such as the reaction with α-diazocarbonyl compounds and in three-component reactions with ethyl diazoacetate and imines …”

Section: Reactions With B- P- and S-based Electrophilesmentioning

confidence: 99%

“…218 The synthetic applications of 172 have been studied, such as the reaction with α-diazocarbonyl com- pounds 218 and in three-component reactions with ethyl diazoacetate and imines. 219 Recently, reagent 170 has been taken as a new source of CF 3 nucleophiles and successfully implemented the coppercatalyzed selective trifluoromethylation of aryl iodides 216,217 and oxidative trifluoromethylation of arylboronates. 220 As an analogue of organotrifluoroborates, 221,222 recent studies show that 170 can also serve as a convenient reagent for nucleophilic trifluoromethylation of nonenolizable aldehydes and Ntosylimines leading to CF 3 -substituted alcohols and N-tosylamines in good yields (Scheme 30).…”

Section: Preparation and Synthetic Applications Of (Trifluoromethyl)t...mentioning

confidence: 99%

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Trifluoromethyltrimethylsilane: Nucleophilic Trifluoromethylation and Beyond

et al. 2014

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Section: Reactions With B- P- and S-based Electrophilesmentioning

confidence: 99%

Section: Preparation and Synthetic Applications Of (Trifluoromethyl)t...mentioning

confidence: 99%

Trifluoromethyltrimethylsilane: Nucleophilic Trifluoromethylation and Beyond

et al. 2014

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“…[40] Dimethyl boronate ester was first converted into CF 3 -substituted borate I by treatment with TMSCF 3 and KF. Salt I was then converted to the corresponding borane II , thus enhancing its electrophilicity towards diazocarbonyls.…”

Section: Carbon-carbon Bond Formationmentioning

confidence: 99%

Transition Metal‐Free ipso‐Functionalization of Arylboronic Acids and Derivatives

Zhu

Falck

2014

Adv Synth Catal

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Arylboronic acids and their derivatives have been widely exploited as important synthetic precursors in organic synthesis, materials science, and pharmaceutical development. In addition to numerous applications in transition-metal-mediated cross-coupling reactions, transition-metal-free transformations involving arylboronic acids and derivatives have recently received a surge of attention for converting the C-B bond to C-C, C-N, C-O, and many other C-X bonds. Consequently, a wide range of useful compounds, e.g., phenols, anilines, nitroarenes, and haloarenes, have been readily synthesized. Amongst these efforts, many versatile reagents have been developed and a lot of practical approaches demonstrated. The research in this promising field is summarized in the current review and organized on the basis of the type of bonds being formed.

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“…With few exceptions,6a,6b,7a a syn / anti mixture of β 2,3 ‐amino esters forms through this method, and the syn adduct is the major diastereoisomer. Recently, a series of 2,3‐diaryl‐3‐amino thioesters have been prepared by a base‐organocatalyzed Mannich reaction of expensive trifluoroethyl arylthioacetates,11 an organocatalytic reduction of enamines,12 or a three‐component reaction of aryl organoboranes, diazoacetate, and imines 13…”

Section: Introductionmentioning

confidence: 99%

syn/anti Switching by Specific Heteroatom–Titanium Coordination in the Mannich‐Like Synthesis of 2,3‐Diaryl‐β‐amino Acid Derivatives

et al. 2014

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A very efficient synthesis of 2,3‐diaryl‐β‐amino acid derivatives is realized by a TiCl4/triethylamine‐catalyzed Mannich‐like reaction of arylacetic or arylthioacetic esters with arylimines. The presence on the arylacetic moiety of an ortho‐heteroatom group able to coordinate to the titanium center is of dramatic importance for the outcome of the reaction and to tune the syn/anti diastereoselection. In particular, with o‐F‐, o‐Cl‐, and o‐Br‐arylacetates, the syn adduct was isolated as the largely prevalent isomer. When (–)‐8‐phenylmenthyl (2‐fluorophenyl)acetate was used, the condensation with imines resulted in high diastereo‐ and enantioselectivity. In agreement with the stereochemical results and NMR studies, a conceivable reaction mechanism was proposed.

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Three-component reactions of CF3-substituted boranes, ethyl diazoacetate and imines

Cited by 7 publications

References 14 publications

Trifluoromethyltrimethylsilane: Nucleophilic Trifluoromethylation and Beyond

Trifluoromethyltrimethylsilane: Nucleophilic Trifluoromethylation and Beyond

Transition Metal‐Free ipso‐Functionalization of Arylboronic Acids and Derivatives

syn/anti Switching by Specific Heteroatom–Titanium Coordination in the Mannich‐Like Synthesis of 2,3‐Diaryl‐β‐amino Acid Derivatives

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