Highly functionalized benzene syntheses by directed mono or multiple magnesiations with TMPMgCl.LiCl.
The direct magnesiation of highly functionalized aromatics bearing an ester, a nitrile, or a ketone can be readily performed by using an OBoc as a directing group and TMPMgCl.LiCl as a base. It allows, for example, the preparation of a meta-magnesiated benzophenone in >95%. After quenching, highly functionalized and substituted benzenes are obtained. [reaction: see text].
Lin
Wenwei
W
Department Chemie und Biochemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, Haus F, 81377 München, Germany.
Baron
Oliver
O
Knochel
Paul
P
D000215:Acylation; D001554:Benzene / Q000138:chemical synthesis*; D001577:Benzophenones / Q000138:chemical synthesis; D002219:Carbamates / Q000138:chemical synthesis; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry; D018021:Lithium Chloride / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*
D001577:Benzophenones; D002219:Carbamates; D007202:Indicators and Reagents; D007659:Ketones; D003300:Copper; D018021:Lithium Chloride; D008274:Magnesium; D001554:Benzene