2001 Fiscal Year Final Research Report Summary
Development of Environmentally Benign Selective Organic Reactions with Allylpolyindium Reagents
| Project/Area Number |
12640515
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Nagoya Institute of Technology |
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Principal Investigator |
ARAKI Shuki Nagoya Institute of Technology, Faculty of Engineering, Professor, 工学部, 助教授 (30115670)
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| Co-Investigator(Kenkyū-buntansha) |
YAMAMURA Hatsuo Nagoya Institute of Technology, Faculty of Engineering, Associate Professor, 工学部, 助教授 (80220440)
KAWAI Masao Nagoya Institute of Technology, Faculty of Engineering, Professor, 工学部, 教授 (60161270)
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| Project Period (FY) |
2000 – 2001
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| Keywords | Indium / Allylation / Polymetalic species / Dianion / Homoallyl alcohol / Homoallylamine / Stereoselectivity / Regioselectivity |
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| Research Abstract |
A novel allylic diindium reagents were synthesized by the reaction of indium metal with 3-bromo-1-iodopropene, which successively coupled with carbonyl compounds and then with aryl, alkenyl or allyl halides in the presence of a Pd(0) catalyst to afford a convenient one-pot synthesis of linear homoallylic alcohols. Thus, a new cascade based on the allylic diindium reagent has been developed.
The di indium reagents, prepared from 3-bromo-1-iodopropene and 4-bromo-2-iodobut- 2-ene, were initially reacted with imines and the resulting vinylindium compounds were then treated with organic halides in the presence of Pd(PPh_3)_4 to give linear N-aryl and N-tosyl homoallylic amines. The diindium from 3-bromo-1-iodopropene is stable in a small amount of water in solvent, whereas the di indium from 4-bromo-2-iodobut-2-ene is easily protonated to give a crotylindium reagent. The reaction of the latter di indium with benzaldehyde gives mainly the 1, 3- and 1, 5-diols via a spontaneous coupling with two molecules of the aldehyde, in contrast to the former which reacts with one molecule of carbonyl compounds to give the vinylindium compounds.
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