N-oxide as a traceless oxidizing directing group: mild rhodium(III)-catalyzed C-H olefination for the synthesis of ortho-alkenylated tertiary anilines.
Double role: A traceless directing group also acts as an internal oxidant in a novel Rh(III) -catalyzed protocol developed for the synthesis of ortho-alkenylated tertiary anilines. A five-membered cyclometalated Rh(III) complex is proposed as a plausible intermediate and confirmed by X-ray crystallographic analysis.
Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry and State Key Laboratory of Biotherapy, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (PR China).
Xiaolei
X
Huang
Jingsheng
J
Huang
Chenglong
C
Du
Xingyi
X
Zhang
Feijie
F
Song
Jingsong
J
You
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D000814:Aniline Compounds; D056831:Coordination Complexes; D016877:Oxidants; D012238:Rhodium
CH activation; anilines; directing groups; olefination