Reactivity of Morita-Baylis-Hillman Adducts in C-H Functionalization of (Hetero)aryl Nitrones: Access to Bridged Cycles and Carbazoles

Ashok Kumar Pandey; Dahye Kang; Sang Hoon Han; Heeyoung Lee; Neeraj Kumar Mishra; Hyung Sik Kim; Young Hoon Jung; Sungwoo Hong; In Su Kim

doi:10.1021/acs.orglett.8b01910

Reactivity of Morita-Baylis-Hillman Adducts in C-H Functionalization of (Hetero)aryl Nitrones: Access to Bridged Cycles and Carbazoles

Ashok Kumar Pandey, Dahye Kang, Sang Hoon Han, Heeyoung Lee, Neeraj Kumar Mishra, Hyung Sik Kim, Young Hoon Jung, Sungwoo Hong, In Su Kim

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

39 Scopus citations

Abstract

The rhodium(III)-catalyzed cross-coupling of (hetero)aryl nitrones with Morita-Baylis-Hillman (MBH) adducts is described. An allylated intermediate derived from aryl nitrones and MBH adducts allows the formation of bridged cyclic compounds via an exotype [3 + 2] cycloaddition. In sharp contrast, electron-rich indolinyl or aniline substrates were found to couple with MBH adducts to generate naphthalene or carbazole derivatives, respectively.

Original language	English
Pages (from-to)	4632-4636
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.8b01910
State	Published - 3 Aug 2018

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title = "Reactivity of Morita-Baylis-Hillman Adducts in C-H Functionalization of (Hetero)aryl Nitrones: Access to Bridged Cycles and Carbazoles",

abstract = "The rhodium(III)-catalyzed cross-coupling of (hetero)aryl nitrones with Morita-Baylis-Hillman (MBH) adducts is described. An allylated intermediate derived from aryl nitrones and MBH adducts allows the formation of bridged cyclic compounds via an exotype [3 + 2] cycloaddition. In sharp contrast, electron-rich indolinyl or aniline substrates were found to couple with MBH adducts to generate naphthalene or carbazole derivatives, respectively.",

author = "Pandey, \{Ashok Kumar\} and Dahye Kang and Han, \{Sang Hoon\} and Heeyoung Lee and Mishra, \{Neeraj Kumar\} and Kim, \{Hyung Sik\} and Jung, \{Young Hoon\} and Sungwoo Hong and Kim, \{In Su\}",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = aug,

day = "3",

doi = "10.1021/acs.orglett.8b01910",

language = "English",

volume = "20",

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journal = "Organic Letters",

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T1 - Reactivity of Morita-Baylis-Hillman Adducts in C-H Functionalization of (Hetero)aryl Nitrones

T2 - Access to Bridged Cycles and Carbazoles

AU - Pandey, Ashok Kumar

AU - Kang, Dahye

AU - Han, Sang Hoon

AU - Lee, Heeyoung

AU - Mishra, Neeraj Kumar

AU - Kim, Hyung Sik

AU - Jung, Young Hoon

AU - Hong, Sungwoo

AU - Kim, In Su

PY - 2018/8/3

Y1 - 2018/8/3

N2 - The rhodium(III)-catalyzed cross-coupling of (hetero)aryl nitrones with Morita-Baylis-Hillman (MBH) adducts is described. An allylated intermediate derived from aryl nitrones and MBH adducts allows the formation of bridged cyclic compounds via an exotype [3 + 2] cycloaddition. In sharp contrast, electron-rich indolinyl or aniline substrates were found to couple with MBH adducts to generate naphthalene or carbazole derivatives, respectively.

AB - The rhodium(III)-catalyzed cross-coupling of (hetero)aryl nitrones with Morita-Baylis-Hillman (MBH) adducts is described. An allylated intermediate derived from aryl nitrones and MBH adducts allows the formation of bridged cyclic compounds via an exotype [3 + 2] cycloaddition. In sharp contrast, electron-rich indolinyl or aniline substrates were found to couple with MBH adducts to generate naphthalene or carbazole derivatives, respectively.

UR - https://www.scopus.com/pages/publications/85050984479

U2 - 10.1021/acs.orglett.8b01910

DO - 10.1021/acs.orglett.8b01910

M3 - Article

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AN - SCOPUS:85050984479

SN - 1523-7060

VL - 20

SP - 4632

EP - 4636

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Reactivity of Morita-Baylis-Hillman Adducts in C-H Functionalization of (Hetero)aryl Nitrones: Access to Bridged Cycles and Carbazoles

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