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| TCI Chemistry News August 2020 | ||||
| TCI offers an extensive catalog of 30,000 high quality organic chemicals suitable for benchtop-to-bulk chemistry. This issue covers our chemistry expertise in diene derivative with high reactivity for Diels-Alder reaction, electron-deficient cyclopentadienyl ligand precursor and its rhodium complex, air-stable tri-tert-butylphosphine equivalent, Simmons-Smith cyclopropanation reaction and more. | ||||
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Diene Derivative with High Reactivity for Diels-Alder ReactionRawal’s diene [B5597] is a building block used in (hetero) Diels-Alder reactions with research showing reactivity of B5597 being 1,000 times higher than the popular Danishefsky-Kitahara diene due to a higher HOMO level of B5597. Additionally, silyl enol ethers can be hydrolyzed under acidic conditions to afford α,β-unsaturated ketones. Because this method is very efficient, we are seeing an increase in B5597’s use in the total syntheses of natural products. | ||||
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Electron-deficient Cyclopentadienyl Ligand Precursor and its Rhodium ComplexD5585 is a precursor of the electron-deficient cyclopentadienyl ligand (CpE) and utilized in the formation of metal complexes with just a few steps. B6169, a rhodium complex, is prepared from D5585 and is a powerful precatalyst for C-H bond activation such as oxidative annulation of anilides with alkynes, and oxidative olefination of anilides with alkenes. | ||||
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Air-Stable Tri-tert-butylphosphine EquivalentWhen using tri-tert-butylphosphine, researchers tend to find unusual and unique reactivity compared to other phosphine ligands due to it being electron rich and its steric bulk. Unfortunately, tri-tert-butylphosphine is incredibly air-sensitive making it difficult to handle. To increase the ease of use, we offer the equivalent tri-tert-butylphosphonium tetrafluoroborate [T2584] that is stable enough to be stored in air for a long period of time. Also, when using tri-tert-butylphosphine in situ as generated from T2584, various other cross-coupling reactions have been facilitated. | ||||
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Simmons-Smith Cyclopropanation ReactionThe Simmons-Smith cyclopropanation reaction is a classic method used to construct a cyclopropane moiety from a parent alkene. The reaction is typically conducted using diiodomethane [D0610] in combination with metallic zinc and copper (Zn/Cu). Zn/Cu can be replaced with diethylzinc [D3214], which is known as the Furukawa modification. The Simmons-Smith reaction has considerable advantages over other cyclopropanation methods as it does not require the use of the highly hazardous diazomethane. In addition, this reaction has a wide functional group tolerance including with alkynes, carbonyls, alcohols, ethers, and also can proceed stereospecifically. | ||||
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