Sulfide‐Catalyzed Trifluoromethylthiolation‐Cyclization of Tryptamine Derivatives

Rui Guo; Baohua Cai; Ming Yu Jin; Huaixue Mu; Jun Joelle Wang

doi:10.1002/ajoc.201900068

Sulfide‐Catalyzed Trifluoromethylthiolation‐Cyclization of Tryptamine Derivatives

Rui Guo^*
, Baohua Cai
, Ming Yu Jin
, Huaixue Mu
, Jun Joelle Wang^*

^*Corresponding author for this work

Department of Chemistry

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

12 Citations (Scopus)

Abstract

Trippy triptamines: An SCF3 group can be incorporated in tryptamine derivatives via a sulfide-catalyzed cascade trifluoromethylthiolation-cyclization. A series of C(3)-CF3S pyrrolidinoindolines were obtained in moderate to good yields under mild conditions. Furthermore, some enantioselectivity was observed when using chiral sulfide thiocineole as a catalyst.

A catalytic method for the incorporation of an SCF3 group to tryptamine derivatives was developed via a sulfide-catalyzed cascade trifluoromethylthiolation-cyclization. A series of C(3)-CF3S pyrrolidinoindolines were obtained in moderate to good yields under mild conditions. Furthermore, some enantioselectivity was observed when using chiral sulfide thiocineole as a catalyst.

Original language	English
Pages (from-to)	687-690
Number of pages	4
Journal	Asian Journal of Organic Chemistry
Volume	8
Issue number	5
Early online date	25 Feb 2019
DOIs	https://doi.org/10.1002/ajoc.201900068
Publication status	Published - May 2019

User-Defined Keywords

organofluorine
trifluoromethylthiolation
cyclization
organocatalysis
pyrrolidinoindolines

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10.1002/ajoc.201900068

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@article{0634d58a7f3c465c9e57b941475fa140,

title = "Sulfide‐Catalyzed Trifluoromethylthiolation‐Cyclization of Tryptamine Derivatives",

abstract = "Trippy triptamines: An SCF3 group can be incorporated in tryptamine derivatives via a sulfide-catalyzed cascade trifluoromethylthiolation-cyclization. A series of C(3)-CF3S pyrrolidinoindolines were obtained in moderate to good yields under mild conditions. Furthermore, some enantioselectivity was observed when using chiral sulfide thiocineole as a catalyst. A catalytic method for the incorporation of an SCF3 group to tryptamine derivatives was developed via a sulfide-catalyzed cascade trifluoromethylthiolation-cyclization. A series of C(3)-CF3S pyrrolidinoindolines were obtained in moderate to good yields under mild conditions. Furthermore, some enantioselectivity was observed when using chiral sulfide thiocineole as a catalyst.",

keywords = "organofluorine, trifluoromethylthiolation, cyclization, organocatalysis, pyrrolidinoindolines",

author = "Rui Guo and Baohua Cai and Jin, \{Ming Yu\} and Huaixue Mu and Wang, \{Jun Joelle\}",

note = "We gratefully thank Shenzhen Basic Research Program (JCYJ20170817110005371) for financial support.",

year = "2019",

month = may,

doi = "10.1002/ajoc.201900068",

language = "English",

volume = "8",

pages = "687--690",

journal = "Asian Journal of Organic Chemistry",

issn = "2193-5807",

publisher = "John Wiley \& Sons Ltd",

number = "5",

}

TY - JOUR

T1 - Sulfide‐Catalyzed Trifluoromethylthiolation‐Cyclization of Tryptamine Derivatives

AU - Guo, Rui

AU - Cai, Baohua

AU - Jin, Ming Yu

AU - Mu, Huaixue

AU - Wang, Jun Joelle

N1 - We gratefully thank Shenzhen Basic Research Program (JCYJ20170817110005371) for financial support.

PY - 2019/5

Y1 - 2019/5

N2 - Trippy triptamines: An SCF3 group can be incorporated in tryptamine derivatives via a sulfide-catalyzed cascade trifluoromethylthiolation-cyclization. A series of C(3)-CF3S pyrrolidinoindolines were obtained in moderate to good yields under mild conditions. Furthermore, some enantioselectivity was observed when using chiral sulfide thiocineole as a catalyst. A catalytic method for the incorporation of an SCF3 group to tryptamine derivatives was developed via a sulfide-catalyzed cascade trifluoromethylthiolation-cyclization. A series of C(3)-CF3S pyrrolidinoindolines were obtained in moderate to good yields under mild conditions. Furthermore, some enantioselectivity was observed when using chiral sulfide thiocineole as a catalyst.

AB - Trippy triptamines: An SCF3 group can be incorporated in tryptamine derivatives via a sulfide-catalyzed cascade trifluoromethylthiolation-cyclization. A series of C(3)-CF3S pyrrolidinoindolines were obtained in moderate to good yields under mild conditions. Furthermore, some enantioselectivity was observed when using chiral sulfide thiocineole as a catalyst. A catalytic method for the incorporation of an SCF3 group to tryptamine derivatives was developed via a sulfide-catalyzed cascade trifluoromethylthiolation-cyclization. A series of C(3)-CF3S pyrrolidinoindolines were obtained in moderate to good yields under mild conditions. Furthermore, some enantioselectivity was observed when using chiral sulfide thiocineole as a catalyst.

KW - organofluorine

KW - trifluoromethylthiolation

KW - cyclization

KW - organocatalysis

KW - pyrrolidinoindolines

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:000472711500019?SID=EUW1ED0B743XgiqgGYM6z5SHHSCuT

U2 - 10.1002/ajoc.201900068

DO - 10.1002/ajoc.201900068

M3 - Journal article

SN - 2193-5807

VL - 8

SP - 687

EP - 690

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 5

ER -

Sulfide‐Catalyzed Trifluoromethylthiolation‐Cyclization of Tryptamine Derivatives

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