Issue 22, 2016
From the journal:

Dalton Transactions

PNPCB heterocycles via thermal and Lewis acid catalyzed trans-hydroborations†

Louie Fana  and  Douglas W. Stephan*a  

* Corresponding authors

a Department of Chemistry, University of Toronto, 80 St George St, Toronto, Ontario, USA
E-mail: dstephan@chem.utoronto.ca

Abstract

The compounds iPr2P(BH3)N31, tBu2PC[triple bond, length as m-dash]CR (R = Ph 2, tBu 3, Cy 4) and Ph2PC[triple bond, length as m-dash]CR (R = Ph 5, tBu 6, Cy 7) were reacted to give the products tBu2P(C[triple bond, length as m-dash]CR)NP(BH3)iPr2 (R = Ph 8, tBu 9, Cy 10) and Ph2P(C[triple bond, length as m-dash]CR)NP(BH3)iPr2 (R = Ph 11, tBu 12, Cy 13). Subsequent thermally induced or Lewis acid catalyzed intramolecular hydroboration of 8 and 11 afforded the PNPCB heterocyclic compounds Ph2P(C[double bond, length as m-dash]CHPh)NP(BH2)iPr214 and tBu2P(C[double bond, length as m-dash]CHPh)NP(BH2)iPr215, respectively. Compounds 8–11 and 13–15 were crystallographically characterized and the mechanisms and implications for the synthesis of inorganic heterocycles are considered.

Graphical abstract: PNPCB heterocycles via thermal and Lewis acid catalyzed trans-hydroborations

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Article information

DOI
https://doi.org/10.1039/C6DT01659F
Article type
Paper
Submitted
28 Apr 2016
Accepted
06 May 2016
First published
09 May 2016

Dalton Trans., 2016,45, 9229-9234

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PNPCB heterocycles via thermal and Lewis acid catalyzed trans-hydroborations

L. Fan and D. W. Stephan, Dalton Trans., 2016, 45, 9229 DOI: 10.1039/C6DT01659F

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