Cu-Catalyzed Cyclization/Coupling of Alkenyl Aldimines with Arylzinc Reagents: Access to Indole-3-diarylmethanes

Rishi R. Sapkota; Raj Kumar Tak; Vivek Aryal; Doleshwar Niroula; Nicholas C. Secosky; Roshan K. Dhungana; Ramesh Giri

doi:10.1021/acs.orglett.2c02531

Cu-Catalyzed Cyclization/Coupling of Alkenyl Aldimines with Arylzinc Reagents: Access to Indole-3-diarylmethanes

Rishi R. Sapkota, Raj Kumar Tak, Vivek Aryal, Doleshwar Niroula, Nicholas C. Secosky, Roshan K. Dhungana, Ramesh Giri

Chemistry

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

1 Scopus citations

Abstract

We report a Cu(II)-catalyzed cyclization/coupling of alkenyl aldimines with arylzinc reagents to create indole-3-diarylmethane derivatives (Sapkota et al. ChemRxiv 2022, DOI: 10.26434/chemrxiv-2022-d6qn). The current reaction provides a unified modular route from readily available starting materials to indole-3-diarylmethanes in which all three arene cores can be decorated with differential functional substitutions on demand. Since the cyclization/coupling of alkenyl aldimines is unknown to date, the current method widens the scope with regard to both the substrate and product diversity for this class of reaction.

Original language	English (US)
Pages (from-to)	6213-6218
Number of pages	6
Journal	Organic Letters
Volume	24
Issue number	33
DOIs	https://doi.org/10.1021/acs.orglett.2c02531
State	Published - Aug 26 2022

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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@article{4b595aba633042008e65fcafc87c5191,

title = "Cu-Catalyzed Cyclization/Coupling of Alkenyl Aldimines with Arylzinc Reagents: Access to Indole-3-diarylmethanes",

abstract = "We report a Cu(II)-catalyzed cyclization/coupling of alkenyl aldimines with arylzinc reagents to create indole-3-diarylmethane derivatives (Sapkota et al. ChemRxiv 2022, DOI: 10.26434/chemrxiv-2022-d6qn). The current reaction provides a unified modular route from readily available starting materials to indole-3-diarylmethanes in which all three arene cores can be decorated with differential functional substitutions on demand. Since the cyclization/coupling of alkenyl aldimines is unknown to date, the current method widens the scope with regard to both the substrate and product diversity for this class of reaction.",

author = "Sapkota, {Rishi R.} and Tak, {Raj Kumar} and Vivek Aryal and Doleshwar Niroula and Secosky, {Nicholas C.} and Dhungana, {Roshan K.} and Ramesh Giri",

note = "Funding Information: We gratefully acknowledge the NSF (CHE-1554299 and CHE-2102394) and The Pennsylvania State University (PSU) for support of this work. We thank Dr. Hemant Yennawar at the Pennsylvania State University for the X-ray crystallographic analysis of compounds 32 and 50 , and Nathaniel Ginder in the Lear group at PSU for help with collecting IR data. The X-ray instrument was funded by NIH SIG S10 grants (1S10OD028589-01 and 1S10RR023439-01). Publisher Copyright: {\textcopyright} 2022 American Chemical Society. All rights reserved.",

year = "2022",

month = aug,

day = "26",

doi = "10.1021/acs.orglett.2c02531",

language = "English (US)",

volume = "24",

pages = "6213--6218",

journal = "Organic Letters",

issn = "1523-7060",

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TY - JOUR

T1 - Cu-Catalyzed Cyclization/Coupling of Alkenyl Aldimines with Arylzinc Reagents

T2 - Access to Indole-3-diarylmethanes

AU - Sapkota, Rishi R.

AU - Tak, Raj Kumar

AU - Aryal, Vivek

AU - Niroula, Doleshwar

AU - Secosky, Nicholas C.

AU - Dhungana, Roshan K.

AU - Giri, Ramesh

N1 - Funding Information: We gratefully acknowledge the NSF (CHE-1554299 and CHE-2102394) and The Pennsylvania State University (PSU) for support of this work. We thank Dr. Hemant Yennawar at the Pennsylvania State University for the X-ray crystallographic analysis of compounds 32 and 50 , and Nathaniel Ginder in the Lear group at PSU for help with collecting IR data. The X-ray instrument was funded by NIH SIG S10 grants (1S10OD028589-01 and 1S10RR023439-01). Publisher Copyright: © 2022 American Chemical Society. All rights reserved.

PY - 2022/8/26

Y1 - 2022/8/26

N2 - We report a Cu(II)-catalyzed cyclization/coupling of alkenyl aldimines with arylzinc reagents to create indole-3-diarylmethane derivatives (Sapkota et al. ChemRxiv 2022, DOI: 10.26434/chemrxiv-2022-d6qn). The current reaction provides a unified modular route from readily available starting materials to indole-3-diarylmethanes in which all three arene cores can be decorated with differential functional substitutions on demand. Since the cyclization/coupling of alkenyl aldimines is unknown to date, the current method widens the scope with regard to both the substrate and product diversity for this class of reaction.

AB - We report a Cu(II)-catalyzed cyclization/coupling of alkenyl aldimines with arylzinc reagents to create indole-3-diarylmethane derivatives (Sapkota et al. ChemRxiv 2022, DOI: 10.26434/chemrxiv-2022-d6qn). The current reaction provides a unified modular route from readily available starting materials to indole-3-diarylmethanes in which all three arene cores can be decorated with differential functional substitutions on demand. Since the cyclization/coupling of alkenyl aldimines is unknown to date, the current method widens the scope with regard to both the substrate and product diversity for this class of reaction.

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SN - 1523-7060

VL - 24

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EP - 6218

JO - Organic Letters

JF - Organic Letters

IS - 33

ER -

Cu-Catalyzed Cyclization/Coupling of Alkenyl Aldimines with Arylzinc Reagents: Access to Indole-3-diarylmethanes

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