The impact of Lewis acid variation on reactions with di-tert-butyl diazo diesters†
Vaibhav
Bedi, 
a
Dipendu
Mandal,
ab
Shi-Ming
Chen,
a
Yile
Wu,
*b
Zheng-Wang
Qu,
*c
Stefan
Grimme
c
and
Douglas W.
Stephan
*ab
a
Dipendu
Mandal,
ab
Shi-Ming
Chen,
a
Yile
Wu,
*b
Zheng-Wang
Qu,
*c
Stefan
Grimme
c
and
Douglas W.
Stephan
*ab
Abstract
Reactions of (tBuO2CN)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 (tBuO2CN)2 with 9-BBN leads to a bicyclic heterocyclic product (tBuOCO(BBN)CN)21. In contrast, the reactions of (tBuO2CN)2 with BF3 or [Et3Si][B(C6F5)4] lead to the isolation of [tBuNHNH2tBu][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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