Alkyl Chalcogenides: Sulfur-based Functional Groups

Heterogeneous gold-catalyzed Sandmeyer coupling of aryldiazonium salts with sodium bromide or thiols for constructing C–Br and C–S bonds

“…It is well known that thiols or thiophenols can react with aryldiazonium salts through an S N Ar mechanism in the presence of a base or a photoredox catalyst. 17 However, one major side reaction of the aryldiazonium decomposition is dediazoniation to form Ar–H. To our delight, in the presence of 3 mol% of MCM-41-2Ph 2 PAuCl, the C–S cross-coupling reaction of 4-methoxyphenyldiazonium tetrafluoroborate ( 1b ) with butane-1-thiol ( 3a ) proceeded smoothly in MeCN at room temperature with Na 2 CO 3 (2.0 equiv.)…”

Denitrative Sulfonylation of Nitroarenes with Sodium Sulfinates

“…This small increase in yield is tentatively attributed to the basic additive sequestering trace acidic impurities (e.g., sulfinic or sulfonic acids), which may be present in the commercial sodium sulfinate salt 7. 14 The versatility of this denitrative sulfonylation protocol was then tested against a range of substrates (Scheme 2). Initial scoping studies revealed that many substrates reacted more sluggishly than nitroarene 1, so reaction times were extended to 24 hours and 2.5 equivalents of sulfinate were used as standard.…”

“…This small increase in yield is tentatively attributed to the basic additive sequestering trace acidic impurities (e.g., sulfinic or sulfonic acids), which may be present in the commercial sodium sulfinate salt 7 . 14…”

Thianthrene Radical Cation as a TransientSETMediator: Photoinduced Thiocyanation and Selenocyanation of Arylthianthrenium Salts†

“…It is noteworthy that the resulting aryl thiocynates and selenocyanates, are not only one of the important chalcogen-containing compounds in the field of pharmaceutical and functional material chemistry [54][55][56][57][58][59][60] (Figure 1c), but also the versatile intermediates for the installation of other organic sulfur/selenium-containing functional groups, such as sulfides/selenides, disulfifides/diselenide, trifluoromethyl thioethers/selenoethers, etc. [61][62][63][64] Moreover, this new process leveraged the versatility, stability, and convenient availability of aryl thiantrenium salts, thus offering a sustainable approach for construction of C-S bond and for the late-stage functionalization bioactive compounds.…”