HFIP Promoted Low-Temperature SNAr of Chloroheteroarenes Using Thiols and Amines

Yuvraj B. Bhujabal; Kamlesh S. Vadagaonkar; Aniket Gholap; Yogesh S. Sanghvi; Rambabu Dandela; Anant R. Kapdi

doi:10.1021/acs.joc.9b02371

HFIP Promoted Low-Temperature S_NAr of Chloroheteroarenes Using Thiols and Amines

Yuvraj B. Bhujabal
, Kamlesh S. Vadagaonkar
, Aniket Gholap
, Yogesh S. Sanghvi
, Rambabu Dandela
, Anant R. Kapdi

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

33 Scopus citations

Abstract

A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base-free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.

Original language	English
Pages (from-to)	15343-15354
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	84
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.9b02371
State	Published - 6 Dec 2019
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "HFIP Promoted Low-Temperature SNAr of Chloroheteroarenes Using Thiols and Amines",

abstract = "A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base-free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.",

author = "Bhujabal, \{Yuvraj B.\} and Vadagaonkar, \{Kamlesh S.\} and Aniket Gholap and Sanghvi, \{Yogesh S.\} and Rambabu Dandela and Kapdi, \{Anant R.\}",

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year = "2019",

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doi = "10.1021/acs.joc.9b02371",

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T1 - HFIP Promoted Low-Temperature SNAr of Chloroheteroarenes Using Thiols and Amines

AU - Bhujabal, Yuvraj B.

AU - Vadagaonkar, Kamlesh S.

AU - Gholap, Aniket

AU - Sanghvi, Yogesh S.

AU - Dandela, Rambabu

AU - Kapdi, Anant R.

PY - 2019/12/6

Y1 - 2019/12/6

N2 - A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base-free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.

AB - A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base-free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.

UR - https://www.scopus.com/pages/publications/85075791062

U2 - 10.1021/acs.joc.9b02371

DO - 10.1021/acs.joc.9b02371

M3 - Article

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AN - SCOPUS:85075791062

SN - 0022-3263

VL - 84

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EP - 15354

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

HFIP Promoted Low-Temperature S_NAr of Chloroheteroarenes Using Thiols and Amines

Abstract

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