One-Pot, Three-Aryne Cascade Strategy for Naphthalene Formation from 1,3-Diynes and 1,2-Benzdiyne Equivalents

Xiao Xiao; Thomas R. Hoye

doi:10.1021/jacs.9b04606

One-Pot, Three-Aryne Cascade Strategy for Naphthalene Formation from 1,3-Diynes and 1,2-Benzdiyne Equivalents

Xiao Xiao, Thomas R. Hoye

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

40 Scopus citations

Abstract

Here we disclose a cascade strategy for naphthyne formation that capitalizes on the traditional benzyne generation (i.e., from an ortho-silyl aryl triflate) and the thermal hexadehydro-Diels-Alder (HDDA) reaction. In this transformation, three distinct aryne species work in tandem, two of which can be formally considered as a 1,2-benzidyne, and each undergoes a different type of trapping event. Many examples were explored by varying the naphthyne capture chemistry as well as the 1,2-benzdiyne equivalent. This strategy enables rapid construction of various naphthalene products and has potential for the synthesis of extended polycyclic arenes.

Original language	English (US)
Pages (from-to)	9813-9818
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	141
Issue number	25
DOIs	https://doi.org/10.1021/jacs.9b04606
State	Published - Jun 26 2019

Bibliographical note

Funding Information:
This work was supported by the National Science Foundation (CHE-1665389). Computations were performed using resources available through the University of Minnesota Supercomputing Institute (MSI). NMR data were obtained with an instrument acquired through the NIH Shared Instrumentation Grant program (S10OD011952).

Publisher Copyright:
© 2019 American Chemical Society.

Publisher link

10.1021/jacs.9b04606

Find It

Find It at U of M Libraries

Cite this

@article{07f6bfa0e13940bc8bae725230b418d0,

title = "One-Pot, Three-Aryne Cascade Strategy for Naphthalene Formation from 1,3-Diynes and 1,2-Benzdiyne Equivalents",

abstract = "Here we disclose a cascade strategy for naphthyne formation that capitalizes on the traditional benzyne generation (i.e., from an ortho-silyl aryl triflate) and the thermal hexadehydro-Diels-Alder (HDDA) reaction. In this transformation, three distinct aryne species work in tandem, two of which can be formally considered as a 1,2-benzidyne, and each undergoes a different type of trapping event. Many examples were explored by varying the naphthyne capture chemistry as well as the 1,2-benzdiyne equivalent. This strategy enables rapid construction of various naphthalene products and has potential for the synthesis of extended polycyclic arenes.",

author = "Xiao Xiao and Hoye, {Thomas R.}",

note = "Funding Information: This work was supported by the National Science Foundation (CHE-1665389). Computations were performed using resources available through the University of Minnesota Supercomputing Institute (MSI). NMR data were obtained with an instrument acquired through the NIH Shared Instrumentation Grant program (S10OD011952). Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = jun,

day = "26",

doi = "10.1021/jacs.9b04606",

language = "English (US)",

volume = "141",

pages = "9813--9818",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "25",

}

TY - JOUR

T1 - One-Pot, Three-Aryne Cascade Strategy for Naphthalene Formation from 1,3-Diynes and 1,2-Benzdiyne Equivalents

AU - Xiao, Xiao

AU - Hoye, Thomas R.

N1 - Funding Information: This work was supported by the National Science Foundation (CHE-1665389). Computations were performed using resources available through the University of Minnesota Supercomputing Institute (MSI). NMR data were obtained with an instrument acquired through the NIH Shared Instrumentation Grant program (S10OD011952). Publisher Copyright: © 2019 American Chemical Society.

PY - 2019/6/26

Y1 - 2019/6/26

N2 - Here we disclose a cascade strategy for naphthyne formation that capitalizes on the traditional benzyne generation (i.e., from an ortho-silyl aryl triflate) and the thermal hexadehydro-Diels-Alder (HDDA) reaction. In this transformation, three distinct aryne species work in tandem, two of which can be formally considered as a 1,2-benzidyne, and each undergoes a different type of trapping event. Many examples were explored by varying the naphthyne capture chemistry as well as the 1,2-benzdiyne equivalent. This strategy enables rapid construction of various naphthalene products and has potential for the synthesis of extended polycyclic arenes.

AB - Here we disclose a cascade strategy for naphthyne formation that capitalizes on the traditional benzyne generation (i.e., from an ortho-silyl aryl triflate) and the thermal hexadehydro-Diels-Alder (HDDA) reaction. In this transformation, three distinct aryne species work in tandem, two of which can be formally considered as a 1,2-benzidyne, and each undergoes a different type of trapping event. Many examples were explored by varying the naphthyne capture chemistry as well as the 1,2-benzdiyne equivalent. This strategy enables rapid construction of various naphthalene products and has potential for the synthesis of extended polycyclic arenes.

UR - http://www.scopus.com/inward/record.url?scp=85067998078&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85067998078&partnerID=8YFLogxK

U2 - 10.1021/jacs.9b04606

DO - 10.1021/jacs.9b04606

M3 - Article

C2 - 31181885

AN - SCOPUS:85067998078

SN - 0002-7863

VL - 141

SP - 9813

EP - 9818

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 25

ER -

One-Pot, Three-Aryne Cascade Strategy for Naphthalene Formation from 1,3-Diynes and 1,2-Benzdiyne Equivalents

Abstract

Bibliographical note

Publisher link

Find It

Other files and links

Fingerprint

Cite this