Double-Carboxylation of Two C-H Bonds in 2-Alkylheteroarenes Using LiO- t-Bu/CsF

Masanori Shigeno; Keita Sasaki; Kanako Nozawa-Kumada; Yoshinori Kondo

doi:10.1021/acs.orglett.9b01386

Double-Carboxylation of Two C-H Bonds in 2-Alkylheteroarenes Using LiO- t-Bu/CsF

Masanori Shigeno, Keita Sasaki, Kanako Nozawa-Kumada, Yoshinori Kondo

PHA - Molecular Pharmaceutical Science

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

6 Citations (Scopus)

Abstract

We describe the double-carboxylation of two C-H bonds (i.e., at the benzylic and the β-positions) in 2-alkylheteroarenes using a combination of LiO-t-Bu and CsF. A diverse range of substrates, namely benzothiophene, thiophene, benzofuran, furan, and indole derivatives, are efficiently converted into the doubly carboxylated products. A variety of functionalities (i.e., methyl, methoxy, halogen, cyano, ester, ketone, and amide moieties) are well tolerated.

Original language	English
Pages (from-to)	4515-4519
Number of pages	5
Journal	Organic letters
Volume	21
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.9b01386
Publication status	Published - 2019 Jun 21

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.9b01386

Fingerprint Dive into the research topics of 'Double-Carboxylation of Two C-H Bonds in 2-Alkylheteroarenes Using LiO- t-Bu/CsF'. Together they form a unique fingerprint.

Cite this

@article{7940b2795ecd4e8c817e48ec8692faf5,

title = "Double-Carboxylation of Two C-H Bonds in 2-Alkylheteroarenes Using LiO- t-Bu/CsF",

abstract = "We describe the double-carboxylation of two C-H bonds (i.e., at the benzylic and the β-positions) in 2-alkylheteroarenes using a combination of LiO-t-Bu and CsF. A diverse range of substrates, namely benzothiophene, thiophene, benzofuran, furan, and indole derivatives, are efficiently converted into the doubly carboxylated products. A variety of functionalities (i.e., methyl, methoxy, halogen, cyano, ester, ketone, and amide moieties) are well tolerated.",

author = "Masanori Shigeno and Keita Sasaki and Kanako Nozawa-Kumada and Yoshinori Kondo",

year = "2019",

month = jun,

day = "21",

doi = "10.1021/acs.orglett.9b01386",

language = "English",

volume = "21",

pages = "4515--4519",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "12",

}

TY - JOUR

T1 - Double-Carboxylation of Two C-H Bonds in 2-Alkylheteroarenes Using LiO- t-Bu/CsF

AU - Shigeno, Masanori

AU - Sasaki, Keita

AU - Nozawa-Kumada, Kanako

AU - Kondo, Yoshinori

PY - 2019/6/21

Y1 - 2019/6/21

N2 - We describe the double-carboxylation of two C-H bonds (i.e., at the benzylic and the β-positions) in 2-alkylheteroarenes using a combination of LiO-t-Bu and CsF. A diverse range of substrates, namely benzothiophene, thiophene, benzofuran, furan, and indole derivatives, are efficiently converted into the doubly carboxylated products. A variety of functionalities (i.e., methyl, methoxy, halogen, cyano, ester, ketone, and amide moieties) are well tolerated.

AB - We describe the double-carboxylation of two C-H bonds (i.e., at the benzylic and the β-positions) in 2-alkylheteroarenes using a combination of LiO-t-Bu and CsF. A diverse range of substrates, namely benzothiophene, thiophene, benzofuran, furan, and indole derivatives, are efficiently converted into the doubly carboxylated products. A variety of functionalities (i.e., methyl, methoxy, halogen, cyano, ester, ketone, and amide moieties) are well tolerated.

UR - http://www.scopus.com/inward/record.url?scp=85067650587&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85067650587&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.9b01386

DO - 10.1021/acs.orglett.9b01386

M3 - Article

C2 - 31150257

AN - SCOPUS:85067650587

VL - 21

SP - 4515

EP - 4519

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 12

ER -