e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron

Investigation of the scope and mechanism of copper catalyzed regioselective methylthiolation of aryl halides

PJA Joseph, S Priyadarshini, ML Kantam, B Sreedhar

Index: Joseph, P.J. Amal; Priyadarshini; Kantam, M. Lakshmi; Sreedhar Tetrahedron, 2013 , vol. 69, # 38 p. 8276 - 8283

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Citation Number: 12

Abstract

Abstract Methylthiolation of structurally diverse aryl halides was accomplished under fluoride free conditions using catalytic amounts of CuI, and DMSO as the methylthiolation source. Optimization studies unveiled several varieties of promoters among which Zn (OAc) 2 was found ideal. The analogous reaction with DMSO-d 6 afforded corresponding deuterated aryl methyl thioether with 99% purity. Mechanistic studies revealed CuSMe as the active ...

4-Bromo-1,3-benzodioxole Structure

4-Bromo-1,3-ben...

Dimethyl sulfoxide Structure

Dimethyl sulfoxide

~76%

5-(METHYLTHIO)BENZO[D][1,3]DIOXOLE Structure

5-(METHYLTHIO)B...

4-Iodotoluene Structure

Dimethyl sulfoxide Structure

Dimethyl sulfoxide

~83%

4-methylthioanisole Structure

4-methylthioanisole

4-Iodobenzonitrile Structure

4-Iodobenzonitrile

Dimethyl sulfoxide Structure

Dimethyl sulfoxide

~75%

4-(Methylsulfanyl)benzonitrile Structure

4-(Methylsulfan...

4-Bromobenzophenone Structure

4-Bromobenzophenone

Dimethyl sulfoxide Structure

Dimethyl sulfoxide

~83%

(4-methylsulfanylphenyl)-phenylmethanone Structure

(4-methylsulfan...

4-Iodoanisole Structure

Dimethyl sulfoxide Structure

Dimethyl sulfoxide

~96%

p-methylthioanisole Structure

p-methylthioanisole

Dimethyl disulfide Structure

Dimethyl disulfide

4-Iodoanisole Structure

~58%

p-methylthioanisole Structure

p-methylthioanisole

dms Structure

4-Iodoanisole Structure

~90%

p-methylthioanisole Structure

p-methylthioanisole

1-Iodo-4-(2-methyl-2-propanyl)benzene Structure

1-Iodo-4-(2-met...

Dimethyl sulfoxide Structure

Dimethyl sulfoxide

~96%

4-tert-Butyl benzyl mercaptan Structure

4-tert-Butyl be...

1-Bromo-4-iodobenzene Structure

1-Bromo-4-iodob...

Dimethyl sulfoxide Structure

Dimethyl sulfoxide

~80%

4-Bromothioanisole Structure

4-Bromothioanisole

1-Iodo-4-nitrobenzene Structure

1-Iodo-4-nitrob...

Dimethyl sulfoxide Structure

Dimethyl sulfoxide

~98%

4-nitrophenyl methyl sulfide Structure

4-nitrophenyl m...

Dimethyl sulfoxide Structure

Dimethyl sulfoxide

1-Bromo-4-nitrobenzene Structure

1-Bromo-4-nitro...

~84%

4-nitrophenyl methyl sulfide Structure

4-nitrophenyl m...

4-Iodobiphenyl Structure

Dimethyl sulfoxide Structure

Dimethyl sulfoxide

~86%

1-methylsulfanyl-4-phenylbenzene Structure

1-methylsulfany...

methyl phenyl sulfoxide Structure

methyl phenyl s...

4-Iodoanisole Structure

~87%

Benzene,1-methoxy-4-(phenylthio)- Structure

Benzene,1-metho...

4-Iodophenol Structure

Dimethyl sulfoxide Structure

Dimethyl sulfoxide

~78%

4-Hydroxythioanisole Structure

4-Hydroxythioanisole

2-Bromopyridine Structure

2-Bromopyridine

Dimethyl sulfoxide Structure

Dimethyl sulfoxide

~71%

2-Methylthio pyridine Structure

2-Methylthio py...

1-Bromonaphthalene Structure

1-Bromonaphthalene

Dimethyl sulfoxide Structure

Dimethyl sulfoxide

~96%

1-methylsulfanylnaphthalene Structure

1-methylsulfany...

Synthesis of 6, 7??methylenedioxy??3, 4??dihydro??1??methylb...

[Ruffin, L. D.; Bowlus, S. B. Journal of Heterocyclic Chemistry, 1983 , vol. 20, p. 461 - 462]

Synthesis of 6, 7??methylenedioxy??3, 4??dihydro??1??methylb...

[Ruffin, L. D.; Bowlus, S. B. Journal of Heterocyclic Chemistry, 1983 , vol. 20, p. 461 - 462]