Catalytic CSe Bond Formation under Very Mild Conditions for the Two‐Step, One‐Pot Synthesis of Aryl Selenoacetates

Abstract

Using the palladium/2-(dicyclohexylphosphino)-2',6'-di(isopropoxy)biphenyl (RuPhos) catalyst, aryl halides and tricyclohexylsilyl selenol can be efficiently coupled to the respective aryl tricyclohexylsilyl selenides. These can be transformed in the same reaction vessel to the corresponding selenoacetates, permitting a straightforward access to a range of molecules potentially useful for materials science applications.

Deposition of MoSe2 flakes using cyclic selenides

“…19 ) and cHex 3 Si–SeH (ref. 20 ) and later also for other silanes as demonstrated in our recent work. 21 Based on these observations, we developed a new synthetic method towards four-membered cycles 6 and 7, which utilizes a direct reaction of elemental selenium with dialkylchlorosilanes in the presence of amine (Method C).…”

“…The crystal product was dried in vacuo. The title compound was prepared from Et 2 SiCl 2 (1.9 ml, 1.99 g, 12.6 mmol) following the Method A (1.9 g, 92%) or Method B (0.9 g, 43% (20), 57 (20).…”

Thiolate versus Selenolate: Structure, Stability, and Charge Transfer Properties

“…96,97 The Se atom was then deprotected by the action of fluoride followed by a reprotection with acetylchloride. A similar approach was used for the synthesis of the thiol compound by modifying previously developed protocols.…”

Towards Volatile Organoselenium Compounds with Cost-Effective Synthesis

“…Encouraged by the easy and high-yielding reaction with Bu3SnH (Scheme 2), we were also curious about a similar reaction with R3SiH. Such a reaction using one equivalent of trialkylsilane provides organoselenium compounds of general formula R3Si-SeH as reported for Et3Si-SeH [20] and cHex3Si-SeH [21]. Hence, we attempted the synthesis of Et3Si-SeH [20], but even after one week at different temperatures (120, 180, 250 °C) the attained yields did not exceed 1% (as monitored by GC/MS).…”