One-Pot Synthesis of 2,3,4-Triarylquinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-chloro-3-iodoquinolines with Arylboronic Acids 英文参考文献.docVIP

Molecules 2010, 15, 7423-7437; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article One-Pot Synthesis of 2,3,4-Triarylquinolines via Suzuki- Miyaura Cross-Coupling of 2-Aryl-4-chloro-3-iodoquinolines with Arylboronic Acids Malose Jack Mphahlele * and Mamasegare Mabel Mphahlele Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa * Author to whom correspondence should be addressed; E-Mail: mphahmj@unisa.ac.za; Tel. +27-12-429-8805; Fax: +27-12-429-8549. Received: 16 September 2010; in revised form: 12 October 2010 / Accepted: 18 October 2010 / Published: 22 October 2010 Abstract: Palladium–catalyzed Suzuki cross-coupling of 2-aryl-4-chloro-3-iodoquinolines with excess arylboronic acids (2.5 equiv.) in the presence of tricyclohexylphosphine afforded the 2,3,4-triarylquinolines in one-pot operation. The incipient 2,3-diaryl-4- chloroquinolines were also prepared and transformed to the primary 4-amino-2,3- diarylquinolines and 2,3-diarylquinolin-4(1H)-ones. Keywords: 2-aryl-4-chloro-3-iodoquinolines; Suzuki-Miyaura cross-coupling; 2,3-diaryl- 4-chloroquinolines; 2,3,4-triarylquinolines 1. Introduction The high reactivity of the aryl-iodo bond toward oxidative addition with palladium in Suzuki [1-4], Sonogashira [4,5], Stille [4] and Heck [4] cross-coupling reactions has been found to allow successive substitution of the halogen atoms (IBr ClF) in dihaloquinolines. The observed trend relates to the Ar–X bond strength, which increases as follows: IBrClF (DPh-X values 65, 81, 96 and 126 Kcal/mol, respectively) and makes the oxidative addition step increasingly difficult [6]. We have previously subjected a series of 2-aryl-4-chloro-3-iodoquinolines to Suzuki cross-coupling with phenylboronic acid (1.2–2.0 equiv.) using tetrakis(triphe