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Updated: Aug 1, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Reactivity of frustrated Lewis pairs with BOC protected diazocarboxylates: FLP capture of diazene
Zahid Hussain1, Yong-An Luo1, Yile Wu1
1Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, Zhejiang, China. wuyile@nbu.edu.cn.
Abstract:
Reactions of (tBuO2CN)2 with FLPs are examined. B(C6F5)3 interacts with the carbonyl oxygen atoms inducing loss of CH2CMe2; however, in the presence of basic donors, the protons are intercepted affording the salts [Hbase]2 [((C6F5)3BO2CN)2] (base = tBu3P 1, NC5H2Ph32, HNC5H6Me43). In contrast, in the presence of (o-Tol)3P, a proton transfers to the diazo-N atom affording (o-Tol)3PN(CO2tBu)NHB(C6F5)34. Further addition of B(C6F5)3 to 4 prompts loss of olefin CH2CMe2 and CO2 affording (o-Tol)3PNHNHB(C6F5)35. The course of these reactions is examined by extensive DFT calculations. The nature of 5 is consistent with the FLP reduction of a diazene fragment.
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