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Monday, 11 May 2015

Zinc diiodide-promoted synthesis of trisubstituted allenes from propargylic amines

Org. Chem. Front., 2015, 2,470-475
DOI: 10.1039/C5QO00047E, Research Article
Jinqiang Kuang, Xinjun Tang, Shengming Ma
Zinc diiodide has been identified as an effective reagent for the efficient synthesis of trisubstituted allenes from propargylic amines.



Jinqiang Kuang,a   Xinjun Tanga and   Shengming Ma*ab  

a
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China
E-mail: masm@sioc.ac.cn
b
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. China
Org. Chem. Front., 2015,2, 470-475

DOI: 10.1039/C5QO00047E, http://pubs.rsc.org/en/Content/ArticleLanding/2015/QO/C5QO00047E#!divAbstract
Zinc diiodide has been identified as an effective reagent for the efficient synthesis of trisubstituted allenes from propargylic amines. Compared to CdI2 this protocol offers a green approach. Due to the easy preparation of propargylic amines through the method developed by this group, this method provides a two-step synthesis of trisubstituted allenes from 1-alkynes, ketones, and pyrrolidine. Finally, an efficient synthesis of such trisubstituted allenes from 1-alkynes, ketones, and pyrrolidine via simple filtration has been developed. Compared with the CdI2-mediated protocol, the current protocol enjoys a much wider scope for ketones and affords functionalized allenes without further cyclization in some substrates.

Thursday, 5 March 2015

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Sunday, 1 March 2015

Synthesis of 2-phenyl indoxyls

Synthesis of 2-phenyl indoxyls 

ARKIVOC 2006 (xi) 37-46 pp. 37 - 46 



Synthesis of 2-phenylindoxyls
Michael C. Hewitt* and Liming Shao
Drug Discovery, Sepracor Inc., 84 Waterford Drive, Marlborough MA 01752, USA
E-mail: michael.hewitt@sepracor.com
http://www.arkat-usa.org/get-file/23564/


Michael HewittMichael hewitt



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10 a  n=1
10a: HPLC Rt = 9.87 min,

1 H NMR (400 MHz, CDCl3)
7.66-7.60 (m, 4H),
7.41-7.37 (m, 3H),
7.11-7.05 (m, 2H),
4.10-4.04 (m, 2H), NCH2
3.69-3.63 (m, 1H), 1H OF OCH2
3.58-3.51 (m, 1H); 1H OF OCH2


13C NMR (100 MHz, CDCl3) 197.2,C=0,  163.9, 137.8, 136.0, 128.9, 128.4, 126.5, 125.7, 122.8, 122.6, 114.8, 99.6, 67.9, 50.1;




http://www.nmrdb.org/13c/index.shtml?v=v2.14.1  PREDICT 13 C NMR

http://www.nmrdb.org/cosy/index.shtml?v=v2.14.1 COSY



GC-MS 13.4 min, M+ 251.

Selected gHMBC couplings (see above): 200 → 7.62, 7.64; 164 → 3.65, 3.5, 7.64; 99 → 3.65, 4.05.



1H NMR PREDICTION BELOW



Michael HewittMichael hewitt



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