75659-50-6

Upstream product

• 7073-94-1 1-bromo-2-isopropylbenzene 
• 19789-33-4 2-isopropylstyrene 
• 19099-54-8 2-isopropyliodobenzene 
• 1066-54-2 trimethylsilylacetylene 
• 1147014-57-0 [(2-isopropylphenyl)ethynyl]trimethylsilane 

Downstream Products

• 1147014-58-1 2-chloro-4-((2-isopropylphenyl)ethynyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine 
• 1147015-00-6 4-((2-isopropylphenyl)ethynyl)-N-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine 

Relevant academic research and scientific papers

1,2-Carbopentafluorophenylation of Alkynes: The Metallomimetic Pull-Push Reactivity of Tris(pentafluorophenyl)borane

We report the novel single-step 1,2-dicarbofunctionalization of an arylacetylene with an allylsilane and tris(pentafluorophenyl)borane [B(C6F5)3] involving C?C bond formation with C?H bond scission at the β-position to the silicon atom of an allylsilane and B→C migration of a C6F5 group. The 1,2-carbopentafluorophenylation occurs smoothly without the requirement for a catalyst or heating. Mechanistic studies suggest that the metallomimetic “pull-push” reactivity of B(C6F5)3 imparts consecutive electrophilic and nucleophilic characteristics to the benzylic carbon of the arylacetylene. Subsequent photochemical 6π-electrocyclization affords tetrafluoronaphthalenes, which are important in the pharmaceutical and materials sciences. Owing to the unique reactivity of B(C6F5)3, the 1,2-carbopentafluorophenylation using 2-substituted furan proceeded with ring opening, and the reaction using silyl enolates formed a C?C bond with C?O bond scission at the silyloxy-substituted carbon.

Br?nsted Acid-Catalyzed Enantioselective Cycloisomerization of Arylalkynes

The first example of an enantioselective carbocyclization of an alkyne-containing substrate catalyzed by chiral Br?nsted acids was achieved. The use of the 2-hydroxynaphthyl substituent on the alkyne as a directing group constituted the key parameter enabling both efficient regioselective protonation of the carbon–carbon triple bond and chiral induction. The key cationic intermediate could be depicted either as a cationic vinylidene ortho-quinone methide or a stabilized vinyl cation. Atropoisomeric phenanthrenes derivatives were produced in high yields and good enantioselectivities under mild, metal-free reaction conditions in the presence of chiral N-triflylphosphoramide catalysts. The carbenic nature of the cationic intermediate was also exploited to describe an example of alkyne/alkane cycloisomerization.

What can13C and1H NMR lithiation shifts tell us about the charge distribution in α-arylvinyllithium compounds?

The energetically stabilizing delocalization of negative electric charge from the Li[sbnd]C(α) bond into the aryl π system of α-arylvinyllithiums, Ar[sbnd]C(Li)[dbnd]CH2, is most efficient with an orthogonal relationship of the aryl ring plane

Regioselective, stereoselective, and conformationally controlled synthesis of(η4-tetraarylcyclobutadiene)(η5- carbomethoxycyclopentadienyl)cobalt metallocenes

The Friedel - Crafts reaction of (η4- tetraphenylcyclobutadiene)(η5-carbomethoxycyclopentadienyl) cobalt with acid chlorides/aluminum chloride resulted exclusively in para-phenyl acylation. Both monoacylated (1.1 equiv of RCOCl/AlCl

One-pot procedure for the synthesis of unsymmetrical diarylalkynes

Unsymmetrical diarylalkynes are accessible by a one-pot procedure from two different aryl halides and (trimethylsilyl)acetylene. The three-component coupling is initialized by a Pd/Cu-catalyzed Sonogashira coupling of an aryl halide with (trimethylsilyl)a

PYRROLOPYRIMIDINE ALKYNYL COMPOUNDS AND METHODS OF MAKING AND USING SAME

Provided herein are pyrrolopyrimide alkynyl compounds, and methods of making and using the same. Such compounds may be used in inflammatory or myeloproliferative disorders. The disclosure also provides for treating cancer.

Platinum and ruthenium chloride-catalyzed cycloisomerization of 1-alkyl-2-ethynylbenzenes: Interception of π-activated alkynes with a benzylic C-H bond

(Chemical Equation Presented) Air-stable and commercially available alkynophilicmetal salts, such as PtCl2, PtCl4, and [RuCl2(CO)3]2, catalyze the cycloisomerization of 1-alkyl-2-ethynylbenzenes to produce substituted indenes even at an ambient temperature. Electrophilically activated alkynes can be intercepted by simple benzylic C-Hbonds at primary, secondary, and tertiary carbon centers. Mechanistic studies, such as labeling studies and kinetic isotope and substituent effects, indicate that the cycloisomerization proceeds through the formation of a vinylidene intermediate and turnover-limiting 1,5-shift of benzylic hydrogen.