Preparation of 15-membered unsaturated N–H containing azamacrocycles and their differential coordination with Pd(0) and Pd(II)

2-(Trimethylsilyl)ethanesulfonamide (TMS(CH2)2SO2NH2 or SES-NH2) - A Sulfonamidation Agent With Multiple Qualities

“…6 SES-NH 2 is considered as an ammonia surrogate for the palladium-catalyzed amination of aryl bromides and aryl chlorides. 6 Moreover, this reagent can be used in iminations reaction, 7 synthesis of azamacrocycles, 8 aza-Baylis-Hillman reaction, 9,10 synthesis of the aziridines 11,12 and important biologically compounds. 12,13 The reagent is commercially available as a white solid (mp 86-89 °C).…”

“…Masllorens et al proposed the synthesis of 15-membered triolefinic azamacrocycles using SES-NH 2 as an amine protecting group [example a)]. An example of removal of the protecting group by fluoride can be verified on second stage of the reaction supplying a good yield of 81% [example b)] 8.…”

2‐(Trimethylsilyl)ethanesulfonyl (or SES) Group in Amine Protection and Activation

“…Except for the synthesis of an (R)-porphyrine, 110,111 linear triamines, 112 and cyclic triamines using SES-NH 2 , 113 the reactions involve primary amines protected by the SES group. The alkylation is efficient in its intermolecular 10,13,46 and intramolecular versions.…”