Facile Synthesis of N-Carboranyl Amines through an ortho-Carboryne Intermediate

Ruofei Cheng; Jie Zhang; Jiji Zhang; Zaozao Qiu; Zuowei Xie

doi:10.1002/anie.201507952

Facile Synthesis of N-Carboranyl Amines through an ortho-Carboryne Intermediate

Ruofei Cheng
, Jie Zhang
, Jiji Zhang
, Zaozao Qiu^*
, Zuowei Xie^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

25 Citations (Scopus)

Abstract

The efficient o-carboryne precursor 1-Li-2-OTf-o-C₂B₁₀H₁₀ reacts with lithium amides at room temperature to give a series of N-carboranyl amines in moderate to high isolated yields. This reaction is compatible with a broad substrate scope from primary to secondary, alkyl to aryl amines. The reaction mechanism is also proposed on the basis of experimental results and DFT calculations. This represents the first general and efficient method for the synthesis of 1-NR¹R²-o-carboranes.

Original language	English
Pages (from-to)	1751-1754
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	5
Early online date	16 Oct 2015
DOIs	https://doi.org/10.1002/anie.201507952
Publication status	Published - 26 Jan 2016

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SDG 9 Industry, Innovation, and Infrastructure

User-Defined Keywords

addition reaction
amination
boron cluster
carborane
carboryne

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10.1002/anie.201507952

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title = "Facile Synthesis of N-Carboranyl Amines through an ortho-Carboryne Intermediate",

abstract = "The efficient o-carboryne precursor 1-Li-2-OTf-o-C2B10H10 reacts with lithium amides at room temperature to give a series of N-carboranyl amines in moderate to high isolated yields. This reaction is compatible with a broad substrate scope from primary to secondary, alkyl to aryl amines. The reaction mechanism is also proposed on the basis of experimental results and DFT calculations. This represents the first general and efficient method for the synthesis of 1-NR1R2-o-carboranes.",

keywords = "addition reaction, amination, boron cluster, carborane, carboryne",

author = "Ruofei Cheng and Jie Zhang and Jiji Zhang and Zaozao Qiu and Zuowei Xie",

note = "This work was supported by grants from the National Basic Research Program of China (973 Program, Grant No. 2012CB821600), National Natural Sciences Foundation of China (No. 21372245 to Z.Q.), Shanghai Pujiang Program (No. 13PJ1410800 to Z.Q.), Youth Innovation Promotion Association CAS (No. 2014230 to Z.Q.), CAS-Croucher Funding Scheme, and NSFC/RGC Joint Research Scheme (N\_CUHK442/14 to Z.X.). We thank Dr. Sunewang R. Wang for helpful discussion. Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

year = "2016",

month = jan,

day = "26",

doi = "10.1002/anie.201507952",

language = "English",

volume = "55",

pages = "1751--1754",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley \& Sons Ltd",

number = "5",

}

TY - JOUR

T1 - Facile Synthesis of N-Carboranyl Amines through an ortho-Carboryne Intermediate

AU - Cheng, Ruofei

AU - Zhang, Jie

AU - Zhang, Jiji

AU - Qiu, Zaozao

AU - Xie, Zuowei

N1 - This work was supported by grants from the National Basic Research Program of China (973 Program, Grant No. 2012CB821600), National Natural Sciences Foundation of China (No. 21372245 to Z.Q.), Shanghai Pujiang Program (No. 13PJ1410800 to Z.Q.), Youth Innovation Promotion Association CAS (No. 2014230 to Z.Q.), CAS-Croucher Funding Scheme, and NSFC/RGC Joint Research Scheme (N_CUHK442/14 to Z.X.). We thank Dr. Sunewang R. Wang for helpful discussion. Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

PY - 2016/1/26

Y1 - 2016/1/26

N2 - The efficient o-carboryne precursor 1-Li-2-OTf-o-C2B10H10 reacts with lithium amides at room temperature to give a series of N-carboranyl amines in moderate to high isolated yields. This reaction is compatible with a broad substrate scope from primary to secondary, alkyl to aryl amines. The reaction mechanism is also proposed on the basis of experimental results and DFT calculations. This represents the first general and efficient method for the synthesis of 1-NR1R2-o-carboranes.

AB - The efficient o-carboryne precursor 1-Li-2-OTf-o-C2B10H10 reacts with lithium amides at room temperature to give a series of N-carboranyl amines in moderate to high isolated yields. This reaction is compatible with a broad substrate scope from primary to secondary, alkyl to aryl amines. The reaction mechanism is also proposed on the basis of experimental results and DFT calculations. This represents the first general and efficient method for the synthesis of 1-NR1R2-o-carboranes.

KW - addition reaction

KW - amination

KW - boron cluster

KW - carborane

KW - carboryne

UR - https://www.scopus.com/pages/publications/84955759788

U2 - 10.1002/anie.201507952

DO - 10.1002/anie.201507952

M3 - Journal article

AN - SCOPUS:84955759788

SN - 1433-7851

VL - 55

SP - 1751

EP - 1754

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 5

ER -

Facile Synthesis of N-Carboranyl Amines through an ortho-Carboryne Intermediate

Abstract

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