Phosphine-mediated formal [5 + 1] aminobenzannulations of Morita-Baylis-Hillman carbonates with isocyanates

Wei Cai; Yanxin Hu; Nan Wang; You Huang

doi:10.1039/d4qo01651c

Phosphine-mediated formal [5 + 1] aminobenzannulations of Morita-Baylis-Hillman carbonates with isocyanates

Wei Cai
, Yanxin Hu
, Nan Wang
, You Huang^*

^*Corresponding author for this work

Nankai University

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

5 Citations (Scopus)

Abstract

Morita-Baylis-Hillman (MBH) carbonates have been widely used in many meaningful annulations. Herein we report the use of an MBH-carbonate-derived relatively long-chained, C5, synthon to enable a formal [5 + 1] annulation with readily available isocyanates. The reaction proceeds via a tandem Wittig and aminobenzannulation process, smoothly constructing both diarylamines and anilines with a broad scope of substrates and excellent chemoselectively.

Original language	English
Pages (from-to)	7130-7135
Number of pages	6
Journal	Organic Chemistry Frontiers
Volume	11
Issue number	24
DOIs	https://doi.org/10.1039/d4qo01651c
Publication status	Published - 11 Oct 2024
Externally published	Yes

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title = "Phosphine-mediated formal [5 + 1] aminobenzannulations of Morita-Baylis-Hillman carbonates with isocyanates",

abstract = "Morita-Baylis-Hillman (MBH) carbonates have been widely used in many meaningful annulations. Herein we report the use of an MBH-carbonate-derived relatively long-chained, C5, synthon to enable a formal [5 + 1] annulation with readily available isocyanates. The reaction proceeds via a tandem Wittig and aminobenzannulation process, smoothly constructing both diarylamines and anilines with a broad scope of substrates and excellent chemoselectively.",

author = "Wei Cai and Yanxin Hu and Nan Wang and You Huang",

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T1 - Phosphine-mediated formal [5 + 1] aminobenzannulations of Morita-Baylis-Hillman carbonates with isocyanates

AU - Cai, Wei

AU - Hu, Yanxin

AU - Wang, Nan

AU - Huang, You

PY - 2024/10/11

Y1 - 2024/10/11

N2 - Morita-Baylis-Hillman (MBH) carbonates have been widely used in many meaningful annulations. Herein we report the use of an MBH-carbonate-derived relatively long-chained, C5, synthon to enable a formal [5 + 1] annulation with readily available isocyanates. The reaction proceeds via a tandem Wittig and aminobenzannulation process, smoothly constructing both diarylamines and anilines with a broad scope of substrates and excellent chemoselectively.

AB - Morita-Baylis-Hillman (MBH) carbonates have been widely used in many meaningful annulations. Herein we report the use of an MBH-carbonate-derived relatively long-chained, C5, synthon to enable a formal [5 + 1] annulation with readily available isocyanates. The reaction proceeds via a tandem Wittig and aminobenzannulation process, smoothly constructing both diarylamines and anilines with a broad scope of substrates and excellent chemoselectively.

UR - https://www.scopus.com/pages/publications/85207398820

U2 - 10.1039/d4qo01651c

DO - 10.1039/d4qo01651c

M3 - Article

AN - SCOPUS:85207398820

SN - 2052-4110

VL - 11

SP - 7130

EP - 7135

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 24

ER -

Phosphine-mediated formal [5 + 1] aminobenzannulations of Morita-Baylis-Hillman carbonates with isocyanates

Abstract

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