The pyridylseleno group in organic synthesis. Part 5. Amidoseleniation of alkenes

Abstract

The reaction of fbmethoxyalkyl 2-pyridyl selenides with acetonitrile in the presence of trifluoromethanesulphonic acid and water affords p-acetamidoalkyl 2-pyridyl selenides in good to excellent yields. This reaction has been used in the two-step amidoseleniation of electron-rich alkenes such as styrene and buta-I ,3-dienes, and of tri-or tetra-substituted alkenes, previously reported as being resistant to amidoselen iation.

Regioselective synthesis of symmetrical pyridyl selenium compounds by bromine–magnesium exchange of bromopyridines using isopropyl magnesium chloride: X‐ray crystal structure of 2,2′,5,5′‐tetrabromo‐3,3′‐dipyridyldiselenide

“…Research on alkyl, aryl and mixed alkylaryl selenides is fast developing and is of immense interest to organic chemists 1,2 and biochemists. 3,4 In contrast, the corresponding pyridyl selenium chemistry, in spite of the greater utility in organic chemistry 5,6 and biochemistry, 7,8 is largely underdeveloped. This is primarily due the non-availability of a convenient synthesis.…”

Synthesis of (−)-Amphidinolide K Fragment C9−C22

“…Alternatively, the primary hydroxy group at C27 could be quantitatively converted into a selenoaryl ether (with 2-nitrophenylselenyl cyanide and Bu 3 P) or, more quickly and without requiring any chromatographic separation, into its 2-pyridylselenyl ether ( 24b ) with di-2-pyridyl diselenide and trimethylphosphine (PySeSePy/Me 3 P) …”

Regioselective Synthesis of Bis(2-halo-3-pyridyl) Dichalcogenides (E = S, Se and Te): Directed Ortho-Lithiation of 2-halopyridines

“…It is curious to note that the chemistry of alkyl, aryl, and mixed alkyl aryl chalcogenides has developed rapidly for the last two decades and is of immense interest to organic chemists [7] and biochemists [8], whereas the chemistry of pyridyl derivatives virtually remained neglected, in spite of its greater utility [9]. Recently, the chemistry of pyridyl derivatives has attracted the attention of the scientific community due to their unique properties, which endear them to the new and exciting applications in organic synthesis.…”