title: Collective Synthesis of 3-Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3-(Methylsulfonyl)indoles from Free (N-H) Indoles via Common N-Indolyl Triethylborate.
abstract: A general and direct C3 functionalization of free (N-H) indoles with readily available electrophiles such as acid chlorides, chloroformates, thionyl chloride, and methylsulfonyl chloride via a common N-indolyl triethylborate intermediate is reported. The reaction proceeds smoothly under mild conditions in up to 93% yield. Indoles with substituents at the C2, C4, C5, C6, and C7 positions are well tolerated. The easy accessibility of a variety of important 3-acylindoles, indole-3-carboxylic esters, indole-3-sulfinic acids, and 3-(methylsulfonyl)indoles demonstrates the high degree of compatibility and practicability of this method.
authors.affiliation: State Key Laboratory Breeding Base-Hebei Province Key Laboratory of Molecular Chemistry for Drug, College of Chemical & Pharmaceutical Engineering, Hebei University of Science & Technology , Shijiazhuang 050018, P. R. China.
authors.forename: Zhi-Wei
authors.initials: ZW
authors.lastname: Zhang
authors.affiliation: State Key Laboratory Breeding Base-Hebei Province Key Laboratory of Molecular Chemistry for Drug, College of Chemical & Pharmaceutical Engineering, Hebei University of Science & Technology , Shijiazhuang 050018, P. R. China.
authors.forename: Hong
authors.initials: H
authors.lastname: Xue
authors.affiliation: State Key Laboratory Breeding Base-Hebei Province Key Laboratory of Molecular Chemistry for Drug, College of Chemical & Pharmaceutical Engineering, Hebei University of Science & Technology , Shijiazhuang 050018, P. R. China.
authors.forename: Hailing
authors.initials: H
authors.lastname: Li
authors.affiliation: State Key Laboratory Breeding Base-Hebei Province Key Laboratory of Molecular Chemistry for Drug, College of Chemical & Pharmaceutical Engineering, Hebei University of Science & Technology , Shijiazhuang 050018, P. R. China.
authors.forename: Huaiping
authors.initials: H
authors.lastname: Kang
authors.affiliation: State Key Laboratory Breeding Base-Hebei Province Key Laboratory of Molecular Chemistry for Drug, College of Chemical & Pharmaceutical Engineering, Hebei University of Science & Technology , Shijiazhuang 050018, P. R. China.
authors.forename: Juan
authors.initials: J
authors.lastname: Feng
authors.affiliation: State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, China Pharmaceutical University , Nanjing 210009, P. R. China.
authors.forename: Aijun
authors.initials: A
authors.lastname: Lin
authors.affiliation: State Key Laboratory Breeding Base-Hebei Province Key Laboratory of Molecular Chemistry for Drug, College of Chemical & Pharmaceutical Engineering, Hebei University of Science & Technology , Shijiazhuang 050018, P. R. China.
authors.forename: Shouxin
authors.initials: S
authors.lastname: Liu