22070-00-4

Upstream product

• 19256-46-3 2-deuteriochlorobenzene 
• 555-16-8 4-nitrobenzaldehdye 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 

Relevant academic research and scientific papers

Iodide as a Nucleophilic Trigger in Aryne Three-Component Coupling for the Synthesis of 2-Iodobenzyl Alcohols

The synthetic potential of KI as the iodide source in aryne three-component coupling has been demonstrated using aldehydes as the third component. This mild and transition-metal-free coupling reaction allowed the straightforward synthesis of 2-iodobenzyl alcohols in moderate to good yields with good functional group compatibility. Moreover, KBr and KCl could be used as the nucleophilic trigger in this aryne multicomponent coupling (MCC) and N-methylisatin and CO2 could be used as the electrophilic third components.

Reaction of μ-Oxobis with Group 14 Propargyl Derivatives and a Propargyl Ether

The treatment of 4,4-dimethyl-1-(trimethylsilyl)-2-pentyne (4a) or 4,4-dimethyl-1-(tributylstannyl)-2-pentyne (4b) with μ-oxobis (2) gives 4,4-dimethyl-1-(2-iodophenyl)-2-pentyne (9).Deuterium labeling has confirmed that propargylation of 2 occurs ortho to the position originally occupied by the I(III).The addition of 2 equiv of 4a to 2 at -80 deg C results in 2 equiv of 9, trimethylsilyl triflate (10), and tert-butylallene (11) and 1 equiv of hexamethyldisiloxane (12); in contrast, the addition of 2 equiv of 4b to 2 at -30 deg C results in 2 equiv each of 9 and tributylstannyl triflate (16).A mechanism that explains these product ratios is proposed.The reaction of 2-o,o'-d2 and 4b shows the negligible intramolecular kinetic isotope effect (0.99 +/- 0.01) expected for what is in effect a Claisen rearrangement.The addition of 2 to 2-butynyl (trimethylsilyl)methyl ether (20) affords the single product 21 resulting from anti addition and control of regiochemistry by the ether oxygen.Attempts to desilylate 21 to an allenyl triflate result in the regeneration of the propargyl ether 20.