Tag: M.W=350-400

Dong, Zhe published the artcileMetallaphotoredox-enabled deoxygenative arylation of alcohols, Computed Properties of 1207294-92-5, the publication is Nature (London, United Kingdom) (2021), 598(7881), 451-456, database is CAplus and MEDLINE.

Metal-catalyzed cross-couplings are a mainstay of organic synthesis and are widely used for the formation of C-C bonds, particularly in the production of unsaturated scaffolds1. However, alkyl cross-couplings using native sp3-hybridized functional groups such as alcs. remain relatively underdeveloped2. In particular, a robust and general method for the direct deoxygenative coupling of alcs. would have major implications for the field of organic synthesis. A general method for the direct deoxygenative cross-coupling of free alcs. must overcome several challenges, most notably the in situ cleavage of strong C-O bonds3, but would allow access to the vast collection of com. available, structurally diverse alcs. as coupling partners4. Authors report herein a metallaphotoredox-based cross-coupling platform in which free alcs. are activated in situ by N-heterocyclic carbene salts for carbon-carbon bond formation with aryl halide coupling partners. This method is mild, robust, selective and most importantly, capable of accommodating a wide range of primary, secondary and tertiary alcs. as well as pharmaceutically relevant aryl and heteroaryl bromides and chlorides. The power of the transformation has been demonstrated in a number of complex settings, including the late-stage functionalization of Taxol and a modular synthesis of Januvia, an antidiabetic medication. This technol. represents a general strategy for the merger of in situ alc. activation with transition metal catalysis.

Nature (London, United Kingdom) published new progress about 1207294-92-5. 1207294-92-5 belongs to benzoxazole, auxiliary class Achiral NHCs Ligands, name is 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate, and the molecular formula is C21H26BF4NO, Computed Properties of 1207294-92-5.

Referemce:
https://en.wikipedia.org/wiki/Benzoxazole,
Benzoxazole | C7H5NO – PubChem

Sakai, Holt A. published the artcileNontraditional Fragment Couplings of Alcohols and Carboxylic Acids: C(sp³)-C(sp³) Cross-Coupling via Radical Sorting, Application In Synthesis of 1207294-92-5, the publication is Journal of the American Chemical Society (2022), 144(14), 6185-6192, database is CAplus and MEDLINE.

In this report, the C(sp³)-C(sp³) cross-coupling of alcs. and carboxylic acids through the dual combination of N-heterocyclic carbene (NHC)-mediated deoxygenation and hypervalent iodine-mediated decarboxylation were described. This mild and practical Ni-catalyzed radical-coupling protocol was employed to prepare a wide array of alkyl-alkyl cross-coupled products, including highly congested quaternary carbon centers from the corresponding tertiary alcs. or tertiary carboxylic acids. Synthetic applications of this methodol. to alc. C1-alkylation and formal homologation, as well as to the late-stage functionalization of drugs, natural products, and biomols. were demonstrated.

Journal of the American Chemical Society published new progress about 1207294-92-5. 1207294-92-5 belongs to benzoxazole, auxiliary class Achiral NHCs Ligands, name is 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate, and the molecular formula is C21H26BF4NO, Application In Synthesis of 1207294-92-5.

Referemce:
https://en.wikipedia.org/wiki/Benzoxazole,
Benzoxazole | C7H5NO – PubChem

Intermaggio, Nicholas E. published the artcileDeoxytrifluoromethylation of Alcohols, Application of 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate, the publication is Journal of the American Chemical Society (2022), 144(27), 11961-11968, database is CAplus and MEDLINE.

Deoxy-functionalization of alcs. represents a class of reactions that has had profound impact on modern medicine. In particular, deoxyfluorination is commonly employed as a means to incorporate high-value fluorine atoms into drug-like mols. Recently, the trifluoromethyl (CF₃) group has garnered attention from medicinal chemists due to its ability to markedly improve the pharmaceutical properties of small mol. drug candidates. To date, however, there remains no general means to accomplish the analogous deoxygenative trifluoromethylation of alcs. Herein, a copper metallaphotoredox-mediated direct deoxytrifluoromethylation is reported, wherein alc. substrates are activated in situ by benzoxazolium salts for C(sp³)-CF₃ bond formation.

Journal of the American Chemical Society published new progress about 1207294-92-5. 1207294-92-5 belongs to benzoxazole, auxiliary class Achiral NHCs Ligands, name is 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate, and the molecular formula is C21H26BF4NO, Application of 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate.

Referemce:
https://en.wikipedia.org/wiki/Benzoxazole,
Benzoxazole | C7H5NO – PubChem

Ma, Xueji published the artcileNHC-alcohol adduct-mediated photocatalytic deoxygenation for the synthesis of 6-phenanthridine derivatives, Recommanded Product: 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate, the publication is Organic & Biomolecular Chemistry (2022), 20(27), 5393-5396, database is CAplus and MEDLINE.

NHC-alc. adduct-mediated deoxygenation of alcs. ROH (R = t-Bu, cyclopentyl, N-bocpiperidin-4-yl, etc.) under photocatalytic conditions is described. This process provides various alkyl radicals, which can react with 2-isocyanobiaryls I (R¹ = H, Me, F; R² = H, Cl; R³ = H, MeO, CF₃; R⁴ = H, F, Me, MeO; R⁵ = H, MeO, CF₃; R⁶ = H, Me, F) to afford 6-substituted phenanthridine derivatives II in moderate to good yields. This method offered the first example of directly using alcs. as radical sources for 6-phenanthridine synthesis.

Organic & Biomolecular Chemistry published new progress about 1207294-92-5. 1207294-92-5 belongs to benzoxazole, auxiliary class Achiral NHCs Ligands, name is 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate, and the molecular formula is C21H26BF4NO, Recommanded Product: 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate.

Referemce:
https://en.wikipedia.org/wiki/Benzoxazole,
Benzoxazole | C7H5NO – PubChem

Bellemin-Laponnaz, Stephane published the artcileSynthesis of N,O-heterocyclic carbene and coordination to rhodium(I) and copper(I), Quality Control of 1207294-92-5, the publication is Polyhedron (2010), 29(1), 30-33, database is CAplus.

5,7-Di-tert-butyl-3-Ph benzoxazolium tetrafluoroborate 1 could be prepared by simple reaction of the corresponding aminophenol with tri-Et orthoformate under acidic conditions. Both rhodium(I) and copper(I) complexes with benzoxazol-2-ylidene ligand were then efficiently synthesized in a straightforward and smooth manner involving the reaction of benzoxazolium salt 1 with metal precursor and an external base. The complexes were fully characterized and used in metal-catalyzed hydrosilylation of ketones, where they showed poor catalytic activity, presumably due to low stability of the complexes under those conditions.

Polyhedron published new progress about 1207294-92-5. 1207294-92-5 belongs to benzoxazole, auxiliary class Achiral NHCs Ligands, name is 5,7-Di-tert-butyl-3-phenylbenzo[d]oxazol-3-ium tetrafluoroborate, and the molecular formula is C21H26BF4NO, Quality Control of 1207294-92-5.

Referemce:
https://en.wikipedia.org/wiki/Benzoxazole,
Benzoxazole | C7H5NO – PubChem