On the competition between six-membered and five-membered NHC towards alane centered ring expansion

被引：6

作者：

Balayan, Kajal ^{[1
,2
]}

Sharma, Himanshu ^{[2
,3
]}

Vanka, Kumar ^{[2
,3
]}

Ravindranathan, Sapna ^{[2
,4
]}

Gonnade, Rajesh G. ^{[2
,3
]}

Sen, Sakya S. ^{[1
,2
]}

机构：

[1] Natl Chem Lab, CSIR, Inorgan Chem & Catalysis Div, Dr Homi Bhabha Rd, Pune 411008, India

[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India

[3] Natl Chem Lab, CSIR, Phys & Mat Chem Div, Dr Homi Bhabha Rd, Pune 411008, India

[4] Natl Chem Lab, Cent NMR Facil, CSIR, Dr Homi Bhabha Rd, Pune 411008, India

来源：

CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 55期

关键词：

N-HETEROCYCLIC CARBENE; BOND ACTIVATION; INSERTION; ADDUCTS; BORANES; COMPLEX;

D O I：

10.1039/d3cc02063k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The combination of 6-SIDipp center dot AlH3 (1) and 5-IDipp resulted in the ring expansion of 6-NHC, while the five-membered NHC remained unchanged, which was subsequently explained by DFT studies. Besides, the substitution chemistry of 1 was also studied with TMSOTf and I-2, which gave rise to the substitution of a hydride by triflate or iodide ligands.

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收藏

页码：8540 / 8543

页数：4

相关论文

共 28 条

[1] Al-H σ-bond coordination: expanded ring carbene adducts of AlH3 as neutral bi- and tri-functional donor ligands [J].

Abdalla, Joseph A. B. ;

Riddlestone, Ian M. ;

Tirfoin, Remi ;

Phillips, Nicholas ;

Bates, Joshua I. ;

Aldridge, Simon .

CHEMICAL COMMUNICATIONS, 2013, 49 (49) :5547-5549

[2] Preparation of Stable Low-Oxidation-State Group 14 Element Amidohydrides and Hydride-Mediated Ring-Expansion Chemistry of N-Heterocyclic Carbenes [J].

Al-Rafia, S. M. Ibrahim ;

McDonald, Robert ;

Ferguson, Michael J. ;

Rivard, Eric .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (43) :13810-13820

[3] The synthesis of a dichloroalane complex and its reaction with an α-diimine [J].

Alexander, Sean G. ;

Cole, Marcus L. ;

Hilder, Matthias ;

Morris, Jonathan C. ;

Patrick, Joanna B. .

DALTON TRANSACTIONS, 2008, (45) :6361-6363

[4] Tertiary Amine and N-Heterocyclic Carbene Coordinated Haloalanes-Synthesis, Structure, and Application [J].

Alexander, Sean G. ;

Cole, Marcus L. ;

Forsyth, Craig M. .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (36) :9201-9214

[5] Hydride-bromide exchange at an NHC-a new route to brominated alanes and gallanes [J].

Alexander, Sean G. ;

Cole, Marcus L. ;

Furfari, Samantha K. ;

Kloth, Marc .

DALTON TRANSACTIONS, 2009, (16) :2909-2911

[6] Alane-Centered Ring Expansion of N-Heterocyclic Carbenes [J].

Anker, Mathew D. ;

Colebatch, Annie L. ;

Iversen, Kalon J. ;

Wilson, David J. D. ;

Dutton, Jason L. ;

Garcia, Lucia ;

Hill, Michael S. ;

Liptrot, David J. ;

Mahon, Mary F. .

ORGANOMETALLICS, 2017, 36 (06) :1173-1178

[7] Beryllium-Induced C?N Bond Activation and Ring Opening of an N-Heterocyclic Carbene [J].

Arrowsmith, Merle ;

Hill, Michael S. ;

Kociok-Koehn, Gabriele ;

MacDougall, Dugald J. ;

Mahon, Mary F. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (09) :2098-2100

[8] A Volatile Dialane Complex from Ring Expansion of an N-Heterocyclic Carbene and Its Use in the Thermal Atomic Layer Deposition of Aluminum Metal Films [J].

Blakeney, Kyle J. ;

Martin, Philip D. ;

Winter, Charles H. .

ORGANOMETALLICS, 2020, 39 (07) :1006-1013

[9] Synthesis and Reactions of N-Heterocyclic Carbene Boranes [J].

Curran, Dennis P. ;

Solovyev, Andrey ;

Brahmi, Malika Makhlouf ;

Fensterbank, Louis ;

Malacria, Max ;

Lacote, Emmanuel .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (44) :10294-10317

[10] Systematic Investigation of the Ring-Expansion Reaction of N-Heterocyclic Carbenes with an Iminoborane Dihydride [J].

Franz, Daniel ;

Inoue, Shigeyoshi .

CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (08) :2083-2087