Halogen Bond-Catalyzed Friedel-Crafts Reactions of Aldehydes and Ketones Using a Bidentate Halogen Bond Donor Catalyst: Synthesis of Symmetrical Bis(indolyl)methanes

Liu, Xuelei1; Ma, Shuang1,2; Toy, Patrick H.1

2019-11-15

10.1021/acs.orglett.9b03578

ORGANIC LETTERS   影响因子和分区

1523-7060

1523-7052

The use of a halogen bond donor to catalyze Friedel-Crafts reactions of indoles with a range of aldehydes and ketones to directly produce bis(indolyl)methanes, including the natural products arsindoline A, arundine, trisindoline, and vibrindole A, is reported. The bidentate catalyst used in these reactions proved to be more effective than a monondentate analogue, a thiourea commonly used as an organocatalyst, and even a trityl cation that has been used previously in the synthesis of bis(indolyl)methanes.

SCI ; IC ; CCR

英语

NI论文

其他

Research Grants Council of the Hong Kong S. A. R., P.R. China[GRF 17307518]

Chemistry

Chemistry, Organic

WOS:000497259500074

AMER CHEMICAL SOC

CHEMISTRY

Web of Science

1.Univ Hong Kong, Dept Chem, Pokfulam Rd, Hong Kong, Peoples R China
2.Southern Univ Sci & Technol, Sch Environm Sci & Engn, Shenzhen 518055, Guangdong, Peoples R China

Liu, Xuelei,Ma, Shuang,Toy, Patrick H.. Halogen Bond-Catalyzed Friedel-Crafts Reactions of Aldehydes and Ketones Using a Bidentate Halogen Bond Donor Catalyst: Synthesis of Symmetrical Bis(indolyl)methanes[J]. ORGANIC LETTERS,2019,21(22):9212-9216.

Liu, Xuelei,Ma, Shuang,&Toy, Patrick H..(2019).Halogen Bond-Catalyzed Friedel-Crafts Reactions of Aldehydes and Ketones Using a Bidentate Halogen Bond Donor Catalyst: Synthesis of Symmetrical Bis(indolyl)methanes.ORGANIC LETTERS,21(22),9212-9216.

Liu, Xuelei,et al."Halogen Bond-Catalyzed Friedel-Crafts Reactions of Aldehydes and Ketones Using a Bidentate Halogen Bond Donor Catalyst: Synthesis of Symmetrical Bis(indolyl)methanes".ORGANIC LETTERS 21.22(2019):9212-9216.