Approach to the synthesis of indoline derivatives from diaryliodonium salts.
An effective method of constructing the indoline moiety via intramolecular nucleophilic ring closure of a diaryliodonium salt is described. Diacetoxyiodoarene compounds (1a-1e) were converted into intermediate Koser's reagent and coupled with arylstannanes (7-10) to form diaryliodonium salts (11a-14e). Indoline compounds with different N-protecting groups, 15, 16, 17, and 18, were synthesized in higher yields by treating salts (11a-14e) with Cs(2)CO(3) and TEMPO. Regardless of the electronic environment of five para-substituted iodoarenes and the natures of four N-protected arylstannane groups, the conversion proceeded well to afford corresponding indolines in yields of 72-84 and 70-84%, respectively.
Department of Chemistry, Sogang University, 35 Baekbeomro Mapogu, Seoul 121-742, Republic of Korea.
Kamalkishor P
KP
Landge
Keun Sam
KS
Jang
Sang Yeul
SY
Lee
Dae Yoon
DY
Chi
D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012492:Salts / Q000737:chemistry; D013237:Stereoisomerism
D006847:Hydrocarbons, Iodinated; D007211:Indoles; D012492:Salts; C057812:indoline