− 6 −CSJ Journal Selects Vol. 2

C–H Activation

Nickel Catalysts/N,N′-Bidentate Directing Groups: An Excellent Partnership in Directed C–H Activation Reactions

Luis C. Misal Castro and Naoto Chatani*Chem. Lett. 2015, 44, 410-421

doi:10.1246/cl.150024

N. Chatani

Highlight Review N,N′-Bidentate Directing Group; Ni Catalyst

The Nickel(II)-Catalyzed Direct Benzylation, Allylation, Alkylation, and Methylation of C–H Bonds in Aromatic Amides Containing an 8-Aminoquinoline Moiety as the Directing Group

Yoshinori Aihara, Jendrik Wuelbern, andNaoto Chatani*Bull. Chem. Soc. Jpn. 2015, 88, 438-446

doi:10.1246/bcsj.20140387

N. ChataniNH

O

N

cat. Ni+ N

H

O

RN

H

R X

R = benzyl, allyl, alkyl, methylX = halogens

Selected Paper N,N′-Bidentate Directing Group; Ni Catalyst

Palladium-catalyzed Annulation of 2-Substituted Silylethynyloxybiaryls through δ-C–H Activation

Yasunori Minami,* Tomohiro Anami, and Tamejiro Hiyama*Chem. Lett. 2014, 43, 1791-1793

doi:10.1246/cl.140725

Y. MinamiH

H

O

O i -PrSi 3

i-Pr3Si

Pd(OAc)2PCy3 O

i-Pr3Si H

O

Sii-Pr3H

toluene (0.1 M)90 °C

Editor's Choice δ-C–H Activation; Pd Catalyst

Development of Cobalt-Catalyzed C–H Bond Functionalization Reactions

Naohiko YoshikaiBull. Chem. Soc. Jpn. 2014, 87, 843-857

doi:10.1246/bcsj.20140149

N. Yoshikai

DG

H

DG

E

ZnX

[Co]

[Co]

[Co]

DG

HDG

+

+

R1

R2

+

E X

Low-valent cobalt catalysis

R1

R2

R1

R2

H ZnXR1

R2

Award Accounts C–H Bond Functionalization; Co Catalyst

Development of Direct Aromatic Coupling Reactions by Transition-Metal Catalysis

Masahiro Miura,* Tetsuya Satoh, andKoji HiranoBull. Chem. Soc. Jpn. 2014, 87, 751-764

doi:10.1246/bcsj.20140099

M. Miura

or

H

YHYH

R

R

R

RR

RR

R

Y

RR

or

Y

R

Ar

YH Ar

or

Ar X

[O]

[O]

Mt

YH: functional groupMt: transition metal

Award Accounts Direct Aromatic Coupling; Pd, Cu, Ni, Rh Catalysts

− 7 − CSJ Journal Selects Vol. 2

Alcohols or Masked Alcohols as Directing Groups for C–H Bond Functionalization

Fanyang Mo, John R. Tabor, andGuangbin Dong*Chem. Lett. 2014, 43, 264-271

doi:10.1246/cl.131154

G. Dong R1

OH HM

catR2

n R1

O HR2

n

or

DGR1

OH FG

R2

n

R1

O FG

R2

n

C–H Functionalization

Highlight Review Alcoholic Directing Group; Pd, Ir, Rh Catalysts

Cu-Catalyzed Aerobic Molecular Transformation of Imine and Enamine Derivatives for Synthesis of Azaheterocycles

Shunsuke ChibaBull. Chem. Soc. Jpn. 2013, 86, 1400-1411

doi:10.1246/bcsj.20130220

S. Chiba

Powered byCu-Catalyzed Aerobic Reactions

"[Cu] + O2"

N

O

NR2

N2

R1

CN

CN

R'

NH

PhCO2Et

NH

NHPh

Ph

Ph

N

NPh

PhPh

HN

PhCO2Et

NN

O

R1

ON

RNN

R'

R

NH

NHPh

Ph Me

N

OPh

Ph

Me

+ R-MgBr

+ R-MgBr

R"

OO

R'

R"

R

NH2

R2

H

N

PhCO2Et H

O

Award Accounts Cu-catalyzed Aerobic Reactions; Azaheterocycles

Cobalt-catalyzed Branched-selective Addition of Aromatic Ketimines to Styrenes under Room-temperature Conditions

Jinghua Dong, Pin-Sheng Lee, andNaohiko Yoshikai*Chem. Lett. 2013, 42, 1140-1142

doi:10.1246/cl.130508

N. Yoshikai

R2 N

PMP

+

CoBr2 (5 mol%)P(4-FC6H4)3 (10 mol%)CyMgBr (50 mol%)

THF, rt, 12–24 h

H+

R1 R3

R2 O

R1 R3

> 20 examples

Letter Aromatic Ketimines ; Co Catalyst

Visible Light-mediated Direct Arylation of Arenes and Heteroarenes Using Diaryliodonium Salts in the Presence and Absence of a Photocatalyst

Mamoru Tobisu,* Takayuki Furukawa, and Naoto Chatani*Chem. Lett. 2013, 42, 1203-1205

doi:10.1246/cl.130547

M. Tobisu rtvisible light

Ar ArI +

NMe

NMe

Ar

with or withoutphotoredox catalyst

Letter Direct Arylation; Diaryl Iodonium Salts

Synthesis of Spirooxindoles from Carbamoyl Chlorides via Cyclopropyl Methine C(sp3)–H Activation Using Palladium Catalyst

Chihiro Tsukano, Masataka Okuno, andYoshiji Takemoto*Chem. Lett. 2013, 42, 753-755

doi:10.1246/cl.130228

C. TsukanoN

R2

O

Pd(OAc)2 (3 mol%)Ad2PnBu (6 mol%)

CO (1 atm), mesitylene120 °C

N

R2

Cl

OR1

R1Cs2CO3 (1.1 equiv)pivNHOH (30 mol%)

40-85%(11 examples)

Editor's Choice C(sp3)–H Activation; Pd Catalyst

− 8 −CSJ Journal Selects Vol. 2

PSiP-Pincer Type Palladium-Catalyzed Dehydrogenative Borylation of Alkenes and 1,3-Dienes

Naohiro Kirai, Shoichiro Iguchi, Tatsuyoshi Ito, Jun Takaya, andNobuharu Iwasawa*Bull. Chem. Soc. Jpn. 2013, 86, 784-799

doi:10.1246/bcsj.20130004

N. Iwasawa Ar2P PAr2

Me

Pd

Si

Bpin

R

R'

or

B2pin2cat. AlEt3

cat. (PSiP )PdOTfR

Bpin

R'Bpin

RBpin

R'Bpin

R

Bpin

Bpin

Bpin

BpinR

(with 2 equiv B2pin2)(with 1 equiv B2pin2)

RR

Active species

BCSJ Award Article Dehydrogenative Borylation; Pd Pincer-type Catalyst