Contrasting reactivity of (boryl)(aryl)lithium-amide with electrophiles: N- vs. p-aryl-C-nucleophilic substitution

Dhara Debabrata; Vijayakanth Thangavel; Nayak Mithilesh Kumar; Kalita Pankaj; Boomishankar Ramamoorthy; Yildiz Cem Burak; Chandrasekhar Vadapalli; Jana Anukul

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Contrasting reactivity of (boryl)(aryl)lithium-amide with electrophiles: N- vs. p-aryl-C-nucleophilic substitution

机译：（硼）（芳基）锂 - 酰胺用电泳的对比反应性：N-与p-芳基-C-亲核代替

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Herein we report two different reactivity modes of lithium(aryl) (boryl)amide, 4, when it is reacted with chlorosilanes such as SiCl4 and MeSiHCl2, and chlorophosphine, Ph2PCl. Thus, the reaction of lithium(aryl)(boryl)amide, 4, with MeSiHCl2 leads exclusively to an N-substitution product, 6. On the other hand, the reaction of 4 with SiCl4 and Ph2PCl proceeds completely differently affording exclusively p-aryl-C-substitution products, 5 and 7, respectively.

机译：在此，当与氯硅烷如SiCl4和MesihCl 2反应时，报告两种不同的反应性模式（芳基）酰胺（硼）酰胺（硼）酰胺，4，以及氯磷脂，pH2PCl反应。因此，锂（芳基）（硼）（硼）酰胺4，用MesihCl2的反应专用于N-取代产物，6.另一方面，用SiCl4和pH2pCl的4与SiCl4和pH2PCL的反应完全不同地进行P-芳基。 -c-c替代产品，5和7。

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《Dalton transactions: An international journal of inorganic chemistry》 |2018年第41期|共5页
作者
Dhara Debabrata; Vijayakanth Thangavel; Nayak Mithilesh Kumar; Kalita Pankaj; Boomishankar Ramamoorthy; Yildiz Cem Burak; Chandrasekhar Vadapalli; Jana Anukul;
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Tata Inst Fundamental Res Ctr Interdisciplinary 21 Brundavan Colony Hyderabad 500075 India;

IISER Dept Chem Dr Homi Bhabha Rd Pune 411008 Maharashtra India;

Tata Inst Fundamental Res Ctr Interdisciplinary 21 Brundavan Colony Hyderabad 500075 India;

HBNI Natl Inst Sci Educ &

Res Bhubaneswar 752050 Odisha India;

IISER Dept Chem Dr Homi Bhabha Rd Pune 411008 Maharashtra India;

Univ Aksaray Dept Med &

Aromat Plants Aksaray Turkey;

Tata Inst Fundamental Res Ctr Interdisciplinary 21 Brundavan Colony Hyderabad 500075 India;

Tata Inst Fundamental Res Ctr Interdisciplinary 21 Brundavan Colony Hyderabad 500075 India;

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正文语种 eng
中图分类化学;无机化学;
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1. Contrasting reactivity of (boryl)(aryl)lithium-amide with electrophiles: N- vs. p-aryl-C-nucleophilic substitution [J] . Dhara Debabrata, Vijayakanth Thangavel, Nayak Mithilesh Kumar, Dalton transactions: An international journal of inorganic chemistry . 2018,第41期

机译：（硼）（芳基）锂 - 酰胺用电泳的对比反应性：N-与p-芳基-C-亲核代替
2. A Qualitative Analysis of a 'Bora-Brook Rearrangement': The Ambident Reactivity of Boryl-Substituted Alkoxide Including the Carbon-to-Oxygen Migration of a Boryl Group [J] . Haruki Kisu, Hirotoshi Sakaino, Fumihiro Ito, Journal of the American Chemical Society . 2016,第10期

机译：'Bora-Brook重排'的定性分析：硼基取代的烷氧基的环境反应性，包括硼基的碳-氧迁移
3. Reactivity of the -C(Cl)=C-C=N- moiety towards AlCl3-induced C-C bond forming reactions: a new synthesis of 7-(hetero)aryl-substituted pyrazolo[ 1,5-a]pyrimidines [J] . Arumugam Kodimuthali, Nishad T. C., Padala Lakshmi Prasunamba Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2009,第3期

机译：-C（Cl）= C-C = N-部分对AlCl3诱导的C-C键形成反应的反应性：7-（杂）芳基取代的吡唑并[1,5-a]嘧啶的新合成
4. Study of heteroaromatic enediyne and substituted benzothiophene synthesis with relative reactivity of substituted aryl iodides in the Sonagashira reaction. [D] . Hossain, Mohammad Selim. 2006

机译：在Sonagashira反应中研究杂芳烯二炔和取代苯并噻吩的合成，以及相对于取代芳基碘的反应性。
5. Boryl substitution of functionalized aryl- heteroaryl- and alkenyl halides with silylborane and an alkoxy base: expanded scope and mechanistic studies [O] . Eiji Yamamoto, Satoshi Ukigai, Hajime Ito 2015

机译：用甲硅烷基硼烷和烷氧基碱取代官能化的芳基杂芳基和烯基卤化物的硼基：扩大的范围和机理研究
6. Boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with silylborane and an alkoxy base: expanded scope and mechanistic studies [O] . Yamamoto, Eiji, Ukigai, Satoshi, Ito, Hajime 2015

机译：用甲硅烷基硼烷和烷氧基碱取代官能化的芳基，杂芳基和烯基卤化物的硼基：扩大的范围和机理研究

Contrasting reactivity of (boryl)(aryl)lithium-amide with electrophiles: N- vs. p-aryl-C-nucleophilic substitution

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