Premium
Cuprate Addition to a 6‐Substituted Pentafulvene – Preparation of sec ‐Alkyl‐Substituted Titanocene Dichlorides and Their Biological Activity
Author(s) -
Cini Melchior,
Bradshaw Tracey D.,
Lewis William,
Woodward Simon
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300474
Subject(s) - chemistry , cyclopentadienyl complex , deprotonation , alkyl , medicinal chemistry , stereochemistry , organic chemistry , ion , catalysis
The copper‐catalysed (10 mol‐% CuBr · SMe 2 , CuCN · LiCl or CuI/PPh 3 ) addition of RMgBr to the pentafulvene 1‐(cyclopenta‐2,4‐dien‐1‐ylidenemethyl)‐2‐methoxybenzene allows the formation of cyclopentadienyl derivatives with α‐CHR(2‐MeOPh) sidechains (R = Me, Et, n Bu, i Bu, allyl, Ph) without H – transfer. The deprotonation of these sec ‐alkyl‐substituted cyclopentadienyls followed by the addition of TiCl 4 allows the isolation of TiCl 2 {η 5 ‐C 5 H 4 CHR(2‐OMePh)} as rac / meso mixtures that show activity against human colon, breast and pancreatic cell lines (GI 50 2.3–42.4 μ M ).