The impact of Lewis acid variation on reactions with di-tert-butyl diazo diesters

被引：1
|
作者：
Bedi, Vaibhav [1 ]
Mandal, Dipendu [1 ,2 ]
Hussain, Zahid [2 ]
Chen, Shi-Ming [1 ]
Wu, Yile [2 ]
Qu, Zheng-Wang [3 ]
Grimme, Stefan [3 ]
Stephan, Douglas W. [1 ,2 ]
机构：
[1] Univ Toronto, Dept Chem, 80 St George St, Toronto, ON M5S 3H6, Canada
[2] Ningbo Univ, Inst Drug Discovery Technol, Ningbo 315211, Zhejiang, Peoples R China
[3] Rhein Friedrich Wilhelms Univ Bonn, Clausius Inst Phys & Theoret Chem, Mulliken Ctr Theoret Chem, Beringstr 4, D-53115 Bonn, Germany
来源：
DALTON TRANSACTIONS | 2024年 / 53卷 / 02期
基金：
加拿大自然科学与工程研究理事会;
关键词：
BASIS-SETS; DENSITY; CAPTURE; REDUCTION; CHEMISTRY; ACCURATE; NITROGEN; DESIGN; COSMO; BOND;
D O I：
10.1039/d3dt03506a
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Reactions of (tBuO(2)CN)(2) with Lewis acids and FLPs have previously been shown to prompt the formation of diazene compounds. In this work, we show that the reaction of (tBuO(2)CN)(2) with 9-BBN leads to a bicyclic heterocyclic product (tBuOCO(BBN)CN)(2) 1. In contrast, the reactions of (tBuO(2)CN)(2) with BF3 or [Et3Si][B(C6F5)(4)] lead to the isolation of [tBuNHNH(2)tBu][BF4] 2 and [tBuN(H)NtBu][B(C6F5)(4)] 3, respectively. The mechanism for the formation of 2 is probed computationally, demonstrating that steric and electronic considerations of the Lewis acid impact the reaction pathway.
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页码：439 / 443
页数：5
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