Corrigendum to: Ligand-Controlled Regiodivergent Pathways of Rhodium(III)-Catalyzed Dihydroisoquinolone Synthesis: Experimental and Computational Studies of Different Cyclopentadienyl Ligands (Chemistry - A European Journal, (2014), 20, 47, (15409-15418), 10.1002/chem.201404515)

Article abstract of DOI:10.1002/chem.202001781

The authors became aware that product 4aa was erroneously assigned to 4-phenyl- 3,4-dihydroisoquinolin-1(2H)-one. Reanalysis of the 1H NMR and 13C NMR spectra of product 4aa confirmed that the correct structure corresponds to the constitutional 3-benzyl-isoindolones isomer (Figure 1). 4-Phenyl-3,4-dihydroisoquinolin-1(2H)-one was reported by Ellman and its structure was confirmed by X-ray crystallographic analysis.[1] The corrected isoindolone structure of 4aa matches all data of 3-benzylisoindolone synthesized by a different route.[2]. (Figure presented.).

Full text of DOI:10.1002/chem.202001781

Corrigendum
doi.org/10.1002/chem.202001781
Chemistry—A European Journal
CORRIGENDUM
M. D. Wodrich, B. Ye, J. F. Gonthier,
C. Corminboeuf,*
The authors became aware that product 4aa was erroneously assigned to 4-phenyl-
1
3,4-dihydroisoquinolin-1(2H)-one. Reanalysis of the H NMR and 13C NMR spectra of
N. Cramer* ..................... 15409–15418
product 4aa confirmed that the correct structure corresponds to the constitutional
3-benzyl-isoindolones isomer (Figure 1). 4-Phenyl-3,4-dihydroisoquinolin-1(2H)-one
was reported by Ellman and its structure was confirmed by X-ray crystallographic
analysis.[1] The corrected isoindolone structure of 4aa matches all data of 3-benzyl-
Ligand-Controlled
Regio-divergent
Pathways of Rhodium(III)-Catalyzed
isoindolone synthesized by a different route.[2]
Dihydroisoquinolone
Experimental and
Synthesis
Computational
–
Studies of Different Cyclopentadienyls
Chem. Eur. J., 2014, 20
DOI: 1002/chem.201404515
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Corrigendum
doi.org/10.1002/chem.202001781
Chemistry—A European Journal
In consequence, the corrected Table 1 reads as follows with the correct structure of
compound 4aa being 3-benzyl-isoindolone instead of 4-phenyl-3,4-dihydroisoquino-
lin-1(2H)-one. The structure of product 3aa as well as all yields and selectivities are
correct.
Table 1. Influence of the different reaction parameters on the divergent
styrene incorporation.[a]
Entry
Rh-cat
Solvent
Total yield [%]
4aa :3aa
1
2
3
4
5
6
7
8
Cp*Rh(OBz)2
Rh1+(BzO)2
Rh2+(BzO)2
Rh3+(BzO)2
Rh4+(BzO)2
Rh5+(BzO)2
Cp*Rh(OBz)2
Cp*Rh(OBz)2
Cp*Rh(OBz)2
Cp*Rh(OBz)2
Cp*Rh(OBz)2
Cp*Rh(OBz)2
Cp*Rh(OBz)2
Cp*Rh(OBz)2
Cp*Rh(OBz)2
Rh2+(BzO)2
Rh2+(BzO)2
Rh2+(BzO)2
EtOH
CH2Cl2
EtOH
EtOH
EtOH
92
73
53
88 :12
1:>99
4 :96
<5 (30% conv.)
8 (45% conv.)
16 (40% conv.)
93
–
50 :50
50 :50
84 :16
82 :18
90 :10
–
60 :40
72 :28
73 :27
60 :40
63 :37
3 :97
EtOH
MeOH
iPrOH
CF3CH2OH
HFIP
toluene
CH2Cl2
acetone
THF
CH3CN
toluene
CH2Cl2
CH3CN
96
9
91 (80% 4aa)[b]
10
11
12
13
14
15
16
17
18
0
94
97
93
99
80
61
76 (72% 3aa)[b]
12 (50% conv.)
6 :94
27:73
[a] Reaction conditions: 0.10 mmol 1a, 0.20 mmol 2a, 5 mol% Rh-catalyst,
0.2 M in the indicated solvent, 238C, 14 h; Yields and ratios were deter-
mined by 1H NMR of the crude product with an internal standard. [b] Iso-
lated yield.
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Corrigendum
doi.org/10.1002/chem.202001781
Chemistry—A European Journal
The analogues series of compounds 4 obtained under the conditions B represent
isoindolones instead of dihydroisoquinolones. The structures of compounds 3 as
well as all yields and selectivities remain identical. The correct Table 2 reads as fol-
lows:
Table 2. Scope for synthesis of dihydroisoquinolones 3 and isoindolones
4.[a]
Table 2. (Continued)
Entry
7
Conditions A
Conditions B
Entry
1
Conditions A
Conditions B
3ba, 72% (94 :6)
4ba, 53% (86 :14)
4ca, 80% (91 :9)
4da, 58% (90 :10)
4ea, 68% (90 :10)
4 fa, 61% (88 :12)
3aa, 72% (94 :6)
4aa, 80% (90 :10)
8
9
2
3
3ca, 63% (94 :6)
3ab, 65% (94 :6)
3ac, 63% (93 :7)
3ad, 68% (>99 :1)
3ae, 63% (96 :4)
3af, 66% (94 :6)
4ab, 74% (90 :10)
4ac, 72% (90 :10)
4ad, 75% (86 :14)
4ae, 75% (86 :14)
4af, 54% (88 :12)
3da, 51% (94 :6)
10
11
3ea, 63% (92 :8); 73% (>99 :1)[b]
4
3 fa, 56% (92 :8); 75% (>99 :1)[b]
[a] Conditions A: 0.10 mmol 1, 0.20 mmol 2, 5 mol% Rh2, 5 mol% (BzO)2,
0.2 M in CH2Cl2, 238C, 14 h. Conditions B: 0.10 mmol 1, 0.20 mmol 2,
5 mol% Cp*Rh(OBz)2, 0.2 M in CF3CH2OH, 238C, 14 h. Isolated yields of
the major isomer. Ratio of 4 :3 was determined by 1H NMR of the crude
product. [b] With 5 mol% Rh1 instead of Rh2.
5
6
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Corrigendum
doi.org/10.1002/chem.202001781
Chemistry—A European Journal
Accordingly, the Supporting Information has been updated with the corrected struc-
tures of compounds 4. All computational data (computed pathways, transition
states and intermediates) obtained for the originally assigned structures 4 are not
affected. The original graphical abstract is misleading as it displays the misassigned
structure on the right. The authors apologize for the error and for any inconven-
ience caused.
[1] T. J. Potter, D. N. Kamber, B. Q. Mercado, J. A. Ellman, ACS Catal. 2017, 7, 150.
[2] M.-W. Chen, Q.-A. Chen, Y. Duan, Z.-S. Yea, Y.-G. Zhou, Chem. Commun. 2012, 48,
1698.
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