Syntheses of ring-fused B-N heteroaromatic compounds

Xiangdong Fang; Hong Yang; Jeff W. Kampf; Mark M.Banaszak Holl; Arthur J. Ashe

doi:10.1021/om058048e

Syntheses of ring-fused B-N heteroaromatic compounds

Xiangdong Fang, Hong Yang, Jeff W. Kampf, Mark M.Banaszak Holl, Arthur J. Ashe

Research output: Contribution to journal › Article › Research › peer-review

60 Citations (Scopus)

Abstract

3a,7a-Azaborindene (14) has been prepared by two multistep syntheses using the Grubbs ring-closing metathesis from appropriate B-vinyl,N-allyl- aminoboranes. 14 was deprotonated by KN(SiMe ₃) ₂ to give 3a,7a-azaborindenylpotassium (5). The reaction of 5 with Cp*ZrCl ₃ afforded the corresponding Zr(IV) complex 18, which on activation with excess methylaluminoxane, forms a good catalyst for the polymerization of ethylene. The reaction of 5 with methylene chloride and BuLi gave 4a,8a-azaboranaphthalene (6), which is isoelectronic and isostructural with naphthalene. DFT calculations on 6 gave a structure that is in good agreement with X-ray diffraction data.

Original language	English
Pages (from-to)	513-518
Number of pages	6
Journal	Organometallics
Volume	25
Issue number	2
DOIs	https://doi.org/10.1021/om058048e
Publication status	Published - 16 Jan 2006
Externally published	Yes

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Cite this

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title = "Syntheses of ring-fused B-N heteroaromatic compounds",

abstract = "3a,7a-Azaborindene (14) has been prepared by two multistep syntheses using the Grubbs ring-closing metathesis from appropriate B-vinyl,N-allyl- aminoboranes. 14 was deprotonated by KN(SiMe 3) 2 to give 3a,7a-azaborindenylpotassium (5). The reaction of 5 with Cp*ZrCl 3 afforded the corresponding Zr(IV) complex 18, which on activation with excess methylaluminoxane, forms a good catalyst for the polymerization of ethylene. The reaction of 5 with methylene chloride and BuLi gave 4a,8a-azaboranaphthalene (6), which is isoelectronic and isostructural with naphthalene. DFT calculations on 6 gave a structure that is in good agreement with X-ray diffraction data.",

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T1 - Syntheses of ring-fused B-N heteroaromatic compounds

AU - Fang, Xiangdong

AU - Yang, Hong

AU - Kampf, Jeff W.

AU - Holl, Mark M.Banaszak

AU - Ashe, Arthur J.

PY - 2006/1/16

Y1 - 2006/1/16

N2 - 3a,7a-Azaborindene (14) has been prepared by two multistep syntheses using the Grubbs ring-closing metathesis from appropriate B-vinyl,N-allyl- aminoboranes. 14 was deprotonated by KN(SiMe 3) 2 to give 3a,7a-azaborindenylpotassium (5). The reaction of 5 with Cp*ZrCl 3 afforded the corresponding Zr(IV) complex 18, which on activation with excess methylaluminoxane, forms a good catalyst for the polymerization of ethylene. The reaction of 5 with methylene chloride and BuLi gave 4a,8a-azaboranaphthalene (6), which is isoelectronic and isostructural with naphthalene. DFT calculations on 6 gave a structure that is in good agreement with X-ray diffraction data.

AB - 3a,7a-Azaborindene (14) has been prepared by two multistep syntheses using the Grubbs ring-closing metathesis from appropriate B-vinyl,N-allyl- aminoboranes. 14 was deprotonated by KN(SiMe 3) 2 to give 3a,7a-azaborindenylpotassium (5). The reaction of 5 with Cp*ZrCl 3 afforded the corresponding Zr(IV) complex 18, which on activation with excess methylaluminoxane, forms a good catalyst for the polymerization of ethylene. The reaction of 5 with methylene chloride and BuLi gave 4a,8a-azaboranaphthalene (6), which is isoelectronic and isostructural with naphthalene. DFT calculations on 6 gave a structure that is in good agreement with X-ray diffraction data.

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