Gram-scale ketone synthesis by direct reductive coupling of alkyl iodides with acid chlorides

Synthesis (Germany)

Volumn 45, Issue 16, 2013, Pages 2234-2240

  Lu, Wenbin ^a   Liang, Zhuye ^b   Zhang, Yuwei ^b   Wu, Fan ^a   Qian, Qun ^a   Gong, Hegui ^a  

^a SHANGHAI UNIVERSITY   (China)

^b ZHENGZHOU UNIVERSITY   (China)

Author keywords

catalysis; halides; ketones; nickel; reductions

Indexed keywords

ACID CHLORIDES; ALKYL IODIDES; ARYL KETONES; COUPLING EFFICIENCY; HALIDES; KETONE SYNTHESIS; REACTION CONDITIONS; REDUCTIVE COUPLINGS;

CATALYSIS; CHLORINE COMPOUNDS; FUNCTIONAL GROUPS; KETONES; NICKEL; REDUCTION;

SYNTHESIS (CHEMICAL);

ACID CHLORIDE DERIVATIVE; ALKYL ARYL KETONE; ALKYL IODIDE DERIVATIVE; CHLORIDE; HALIDE; HALOGENOALKANE; IODINE DERIVATIVE; NICKEL; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); CROSS COUPLING REACTION; CYCLIZATION; GRAM SCALE PREPARATION; REDUCTION KINETICS; SYNTHESIS;

EID: 84881481474     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0033-1339297     Document Type: Article

References (10)

1. For reviews and selected examples, see: (a) Johnson, J. B.; Rovis, T. Acc. Chem. Res. 2008, 41, 327
2. Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z. Angew. Chem., Int. Ed. Engl. 1987, 26, 1157
3. Reddy, C. K.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1700.
4. Wu, F.; Lu, W.; Qian, Q.; Ren, Q.; Gong, H. Org. Lett. 2012, 14, 3044.
5. Yin, H.; Zhao, C.; You, H.; Lin, K.; Gong, H. Chem. Commun. 2012, 48, 7034.
6. For notable similar works on the coupling of alkyl halides with alkanoic acid derivatives, see: (a) Wotal, A. C.; Weix, D. J. Org. Lett. 2012, 14, 1476
7. d'Incan, E.; Sibille, S.; Périchon, J.; Moingeon, M.-O.; Chaussard, J. Tetrahedron Lett. 1986, 27, 4175
8. Onaka, M.; Matsuoka, Y.; Mukaiyama, T. Chem. Lett. 1981, 10, 531.
9. Steib, A. K.; Thaler, T.; Komeyama, K.; Mayer, P.; Knochel, P. Angew. Chem. Int. Ed. 2011, 50, 3303.
10. Cai, L.; Zhao, H.; Zhang, W.; Dai, L. WO 2010127574, 2010.