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Breit, B., Science of Synthesis, (2007) 25, 277.
General Introduction
The formal addition of a C—H bond of formaldehyde across the C=C bond of an alkene function is referred to as the hydroformylation of alkenes.[1,2] In practice, instead of formaldehyde a mixture of hydrogen and carbon monoxide (syngas) is usually employed that adds to an alkene function in the presence of a suitable transition-metal catalyst (Scheme 1). Synthetically, a one-carbon chain extension is achieved with simultaneous introduction of the aldehyde function. Thus, all atoms of the starting materials become an integral part of the product, which fulfills the criterium of an ideal atom-economic reaction.[3,4] Owing to its industrial importance,[5] this reaction has been reviewed extensively.[6–29] The purpose of this particular chapter is to summarize the hydroformylation reaction with respect to its utility and applicability to laboratory-scale organic synthesis.
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Meeee | Meeeeeeee | Mee |
---|---|---|
eeeeeee eeeeee | M8M(MM8)8 | [88] |
eeeeeee | M8MeM88 | [88] |
eeeee eeeeeeeee | M8MM8 | [88] |
eeeeeeee eeeeee | M8M8M8M | [88] |
eeeeee | [88] | |
eeeeeeeeee | M8MMMM8M8 | [88] |
8-eeeeeeeeeeeeeeeeeee | M8MMMe | [88] |
eeeeeeeee | [88] | |
eeeeeeee | [88] | |
eeeeeeeeee | M8MM88 | [88] |
eeeeeeeeee | M8MM(MM8)8 | [88] |
eeeeeeee | M8MM | [88] |
eeeeee | M8MM8 | [88] |
eeeee eeeeee | M8MMeM88 | [88] |
eeeeeeee | M8MM8 | [88] |
8-eeeeeeeeeeeeeeeee | M8MMe | [88] |
eeeee eee eeee eeeeeee | M8M (M = M, Me, Me, M) | [88] |
eeeeeeee | M8MM | [88] |
eeeeeeeee | M8MMM | [88] |
eeeeeee | M8M(MM8)MM8 | [88] |
eeeeeee | M8M(M)M8 | [88] |
eeeeee | M8M8M(MM8)MM8 | [88] |
eeeeeeeeee eeeee | M8MM8M | [88] |
eeeeeeeeee eeee eeeeee | M8MM8M8 | [88] |
eeeeeeee eeeeee | M8M(M)MM8M8 | [88] |
Mee eeee ee eeeeee eeeeeeeeeeeeeeee eeeeeee eeee eeeeeeeeeeeee ee eee eeeeeeeeeeee eeeeeee ee eee eeeeee. Mee eeeee ee eeeeee eeeeeeeeee eee eeee eeeeeeeeee eee eeeeeeeeee eeeeee eee eeeeeee eeeeeeeee eee eeeeeeee eeee eee eeeeeeeee eee eeeeee-eeeeeeee eeeeeee eeeeeeeee ee e eeeeeeeeeee eeeee.[88,88] Meee, e eeeeee eeeeeeeeeee eeee ee eeeeee eeeeeeeeee eeee eee eeeeee ee eeeeeeeeeeee ee eee M=M eeee eee eeee eeeee (Meeee 8). Mee eeeee-eeeeeeee eeeeeee eeee eeeeeee eeeeeeeeeeeeeeee eee eeeeeeeeee eeeeeeee eeeeeee, e.e. eeeeeeeeeeeeee eeeeeeeeeee. Meeeeeeeeee, eeeeeeeeeeee eee eeee eeeeeeee eeee eeeeeee eeeeeee. Meeeeeeeeeeeeeee M=M eeeee eee eeeeeeeee eeeee eeeeee eeeeeeeeeeeeeeee.
Meeee 8 Meeeee ee Meeeee Meeeeeeeeeee Meeeeee ee Meeeeeeeeeeeeeee Meee[88,88]
Meeeee | Meeeeeee Meee (8888 e·eee−8) | Mee |
---|---|---|
88.8 | [88,88] | |
88.8 | [88,88] | |
8.88 | [88,88] | |
8.88 | [88,88] | |
8.88 | [88,88] |
Meeeeeeeeeee, e eeeeeeeeee eeeee ee Meeeeeeee'e eeeeeeeeeeeeeeee eeeeeeee, eeeeeeeeeeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeee(M), eeeeeee e eee ee eeeeeeeeeeee eeeeeee eeeeeee eeeee eeeeeeee eeeeeeeeeee ee eeeeeeee eeeeeeeeeeee (Meeee 8).[88,88]
Meeee 8 Meeeeeee Meeee ee Meeeeeeeeeeeeeee ee Meeeeeeeeee Meeeeeeeee Meeeeeeee Meeeeeeeeeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeee(M) ee Meeeeeee[88,88]
Meeeee | Meeeeeee Meeee | Mee |
---|---|---|
8.88 | [88,88] | |
8.88 | [88,88] | |
8.88 | [88,88] | |
8.88 | [88,88] | |
8.88e | [88,88] | |
8.88 | [88,88] | |
8.88 | [88,88] | |
8.88 | [88,88] | |
8.88 | [88,88] | |
8.88 | [88,88] | |
8.88 | [88,88] | |
8.88e | [88,88] | |
8.88 | [88,88] | |
8.88 | [88,88] | |
8.88 | [88,88] | |
8.88 | [88,88] | |
8.88 | [88,88] | |
8.88 | [88,88] | |
8.88 | [88,88] | |
8.88 | [88,88] | |
8.88e | [88,88] | |
8.88 | [88,88] | |
<8.88 | [88,88] | |
<8.88 | [88,88] | |
<8.88 | [88,88] |
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Mee eeeeeeeeee ee eeeeeeeeeeeeeeee eeeeeeeee ee eeeeee 8 eee eeeeeeee 88 eeeeeeeee eee eeeeeeee ee Meeeee 8.[88,88,88] Meee, eeeeeeee eeee eeeeeee(M) eeeeeee eeeee eeeeee eeeeeeee eee ee eee eeeeeeee ee eeeee eeeeeee M eeee ee eeeeeeeeee eeeee eeeeeee eee eeeeee eeeeeeee, e eeeeeeee eeeeeeeeeee eeeeeee 8 ee eeeeee ee e eee eeeeeeeeeeee. Meeeeeeeeeee ee e eeeeee eeeeeeee eeeeee eeeeeeeee eee eeeeeeeeeeeeee eeeeeeeeeee 88-eeeeeee-eeeeeeee eeeeeee 8. Mee eeee eeeeeeee eeeee eeeeee eeee eee eeeeeeeeeeee ee eee eeeeee eeeeeeeee 8 ee eeee eee eeeeeeee eeeeeeeeeee eeeeeee eeeeee eeeeeee 8, eeee eee eeeeee eeeeeeeee ee eeeeeeeeee eeeeeeee. Meee eeee ee eeeeeeee ee eeeeee eeeeeeeee eeee eee Me—M eeee (eeeeeeeeeeeeeee) ee eeee eeeeeeee eeeeeeeeee eeeeeeeeeeee eeeeeeeee 8 eee 88. Meeeeeeeee eeeeeeeeeeee ee eeeeee eeeeeeee ee eeeee eeeeeeeee eeeeee eeeeeeee eeeeeeeeeee eeeeeeeee 8 eee 88, eeeeeeeeeeee, eeeee eee eee eeeee eee eeeeeeeee eeeeeeeee ee eee eeeee eeeeeeeeeee ee eee ee eee eeeeeeeeeee eeeeee eeeeeeee eeeeeee ee eeee eee eeeeeeeeee eeee eeeeeeeee 8 eee 88. Meeeeee, eeeeeeeee eeeeeeee ee eeeeeeeeee ee eeee 8 eee 88, eeeeeeee ee eeeeeeeee eeeeeeeeeee, eeeeeeeee eee eeeeeeee eeeeeeeee 8 eee 88, eeeeeeeeeeee, eee eeeeeeeeeee eee eeeeeeee 8.
Meeeee 8 Meeeeeeeeee Meeeeeeeeee eee eee Meeeeee-Meeeeeeee Meeeeeeeeeeeeeee ee Meeeeee[88,88,88]
Meeeeee eeeeeee eeeeeeeee eeee e eeeeeeeeeeeeeeeeee-eeeeeeee eeeeeee eeeeeeee eeeeeeee eeee eeee eee eeeeeeeeee eeee eeeeeeeee eeeeeee, eeee ee eeeeee eee eeeeeee, eee eeee-eeeeeeeeeee eeee ee eeeee ee eee eeeeeeeee eeeee, eee eeee eee ee eeeeee eee eeeeee eeeeeeee ee eeeeeeeee eeee.[88] Meeeeeeeeeeeeeeeee eeeeeeeeeee eeeeeeeee e eeeeeee–eeeeeeeeeee eeeeeeee eee eee-8-eee ee eee eeeeeeeee eeee eeeee eeee eeeeee eeeeeeeee eeee eee Me—M eeee ee eeeeeeeeeeee eeee eeeeeee ee eee eeeeeeeee ee eee eeeeee eeeeeeeeeeee eeeeeee 8 (e.e., eeeeeeeee eeee eeeeeeee ee Meeeee 8).[88,88] Meeeeee, eeee eeee eee eeeeee eeeeeeeeee eee eee eeeeeeeee ee eee eeeeeeee eeeeeeeeeeee eeeeeee 88, eeeee eeeeeee ee eee eeeeeeee eeeeeeeeee eee eee eeeeee ee eee eeeeee.
Mee eeeeeeeeeeeeeeee ee eee eeeeeeeeeeeeeeee eeeeeee ee e eeeeee ee eeeeeee.[88] Meeee eeeeeee eeeeeeee eeeeeeeee eeeeeeeeeee eeee eee eee ee eee eeeeeeeee eeeeeeeeeee eee eeeeeeeeeeee ee eee eeeeeeee eeeeeeeeeeeeeee eeeeeeee 8 eee 88 (Meeeee 8). Meeeeeeeeee, eeeeeeeee eeeeeee eeeeeee ee eeeeeeeeee eeeeee eeee eee eeee ee eee eeeeeeeee eeee ee ee eeeeeeeeee, eeeee eeee eee eeeeeeee eeeeeeeee eeeeeeeee eeeeeeeeeee. Meeeeee, eee eeee eeeeeeeeeee, eee eeeeeee eeeeeee ee eee eeeeeeee. Meee eeeeeeeee ee eeeeeeeeeeee eeeee ee eeeeee-eeee eeeeeee eeee eeeee eee eeeeeeeeee eeeeeee ee eee eeeeeeeeeeeee eeeeee eeeee eeeeee. Me eeeeee eeeee eeeeeeeeeeee eeeeeee ee eeee eeeeeeeeeee eeeeeee ee eeeeeee eee eeeeeeeeeeeeeeee ee eeeeee, ee ee eeeeeeeeee ee eeeeeeee eee eeeeeeeeeeee eeeee eeeeee eeeeeee eeeeeeeeee (Meeeee 8).[88,88]
Meeeee 8 Meeeeeeeeeeeeeee Meeeee ee Meeeeeeeeeeeeeee eee Meeeeeeee Meeeee Meeeeee[88,88]
Meee, eeeeeeeeeeeeeeee eeeeeee ee eeeeeeeee eeee e eeeeeee eee eee eeeee eee eeeeeee ee eeeeeee: eeeeeeee eee 8,8-eeeeeeeeeeeee eeeeeee. Meee 8,8-eeeeeeeeeeeee eee eeeeeeeeeeeeee eeeeeee eeeeeeeee eeeeeee eeee eee eeeeeeeeeeeee eeeeeee eeeee ee Meeeeeeee' eeee, eeeee eeeeee eeee eee eeeeee eeeee ee eeeeeeee eeee ee ee eeeee eee eeeeeeeee ee e eeeeeeeeee eeeeee eeee.[88] Meeee, eeee eeeeeeeee eeeee eee eee eeeeeeeee eeeeeeeee ee eeeeee eeeeeeeee eeee eeeeeeeeeeeeeeee ee eeeeeeee eeeeeee. Mee eeeeeeee eeeeeeeeeeeeeeee ee eeeee ee eee eeeeeeee eeeeeeee, ee eeeeeeeeee eeeeeeeee eeeeee eeeee-eeeeeeeeeee eeeeeee, ee ee eeeeeeee eeeeeee. Meee eeee eeeeeeeee ee eee eeeeeeeeeeeeeee eeeeeeeeeeeeeeee ee eeeeeeeeeeeeeee 8,8-eeeeeeeeeeeee eeeeeee. M eeeeeee eeeeeeee ee eeee eeeeeee eeee eee eeeee ee eeeeeee.[88]
References
[1] | Meeeee, M., MM 8 888 888, (8888); Meee. Meeee., (8888) 88, 888. |
[2] | Meeeee, M., MM 888 888, (8888). |
[3] | Meeee, M. M., Meeeeee (Meeeeeeeee, M. M.), (8888) 888, 8888. |
[4] | Meeee, M. M., Meeee. Meee., (8888) 888, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
[5] | Meeeeeeeee, M.; Meee, M.-M., Meeeeeeeee Meeeeee Meeeeeeee, Meeee-MMM: Meeeeeee, Meeeeee, (8888); e 888. |
[6] | Meeee, M. M. M.; eee Meee, M.; Meeeeeeeee, M. M.; eee Meeeeee, M. M. M. M., Meeee. Meee. Mee., (8888) 888, 8888. |
[7] | Meeeee, M.; Meeeee, M.; Meeeeee, M.; Meee, M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
[8] | Meeee, M. M.; Meee-Meeeeeee, M. M.; Meee, M. M.; Meeeeeeeee, M. M.; Meeeee, M. M., M. Meeeeeeee. Meee., (8888) 888, 8888. |
[9] | Meeeee, M.-M.; Meeeeee, M., Mee. Meeee., (8888) 88, 8. |
[10] | Meeee, M., Mee. Meee. Mee., (8888) 88, 888. |
[11] | Meeee, M.; Meeeee, M., Meeeeeeee, (8888), 8. |
[12] | Meeee, M.; Meee, M.-M.; Meeeeeeeeeeee, M.; Meeeeeee, M., Mee. Meeee. (M. M.), (8888) 88, 8. |
[13] | eee Meeeeee, M. M. M. M.; Meeeee, M., Meeeeee Meeeeeeee Meeeeeeeeeeeeeee, Meeeee: Meeeeeeee, (8888). |
[14] | Meeeeee, M.; Meeà, M.; Meeeeeee, M., Meee. Mee., (8888) 888, 888. |
[15] | eee Meeeeee, M. M. M. M.; Meeee, M. M. M.; Meee, M. M. M.; Meeeeee, M., Meee. Mee., (8888) 888, 8888. |
[16] | Meeeeeeee, M.; Mäeeeeeee, M.; Meee, M.; Meeeeeee, M.; Meeeee-Meeeeee, M. M.; Meeeeeeee, M. M.; Meeeee, M.; Meeeeeeeee, M.; Meeeeee, M., Meee. Mee., (8888) 88, 8888. |
[17] | Meeeeee-Meeee Meeeeeeeeeeeee Meeeeeeee: Meeeeeee eee Meeeeeeeeeee, Meeeeeee, M. M.; Meeeeee, M., Mee.; Meeee-MMM: Meeeeeee, Meeeeee, (8888). |
[18] | Meeeeeee, M. M.; Meeeeee, M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 8888. |
[19] | Meeeeeee, M. M.; Meeeeeeeeeee, M. M., Me Meeeeee Meeeeeeeeee Meeeeeeee eeee Meeeeeeeeeeeee Meeeeeeee, Meeeeee, M.; Meeeeeee, M. M., Mee.; MMM: Meeeeeee, Meeeeee, (8888); e 88. |
[20] | Meeeee, M.; Meeeeee, M.; Meeeeeee, M. M.; Meeeeeeeeeee, M. M., M. Mee. Meeee. M: Meee., (8888) 888, 88. |
[21] | Meeee, M.; Meeeee, M.; Meeeeeeeeeeee, M., Me Meeeeeeeeeeee Meeeeeeeeeeeee Meeeeeeee MM, Meee, M. M.; Meeee, M. M. M.; Meeeeeeee, M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 88, e 8. |
[22] | Meeeeeeee, M., Me Meeeee–Meee, (8888); Mee. M 88e, e 8888. |
[23] | Meeeee, M. M., Me Meeeeeeeeeeee Meeeeee Meeeeeeee, Meeee, M. M.; Meeeeee, M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8, e 888. |
[24] | Meeee, M.; Meeee, M.; Meeee, M., Mee. Meeeeeeee. Meee., (8888) 88, 888. |
[25] | Meéeeee, M.; Màeeee, M.; Meeeee, M., Meeeeeeeeee: Meeeeeeee, (8888) 88, 8888. |
[26] | Meeeee, M.; Meeee, M., Me Meeeeeeee Meeeeeeeee Meeeeeeee, 8ee ee., Meeee, M., Me.; Meeee-MMM: Mee Meee, (8888); e 888. |
[27] | Meeeeeee, M.; Meeeeeeee, M.; Meeeeeeee, M., Meeeeeeee, (8888) 8, 888. |
[28] | Meeeeeee, M.; Meeeeeeeee, M.-M.; Meeeeeee, M., Meee. Mee., (8888) 88, 8888. |
[29] | Meeeeeee, M.; Meeee, M. M.; Meeeee, M., Meeeeeeeeee: Meeeeeeee, (8888) 8, 8888. |
[30] | Meeee, M. M.; Meeeee, M. M.; Meeeeeeee, M., M. Meee. Mee. M, (8888), 8888. |
[31] | Meeee, M. M.; Meeeeeeee, M., M. Meee. Mee. M, (8888), 8888. |
[32] | Meeeeeeee, M., Meee. Mee. Meee. Me., (8888), 8888. |
[33] | Meeeee, M. M.; Meeeeee, M. M.; Meeee, M. M.; Meeeeeeee, M., M. Meee. Mee. M, (8888), 8888. |
[34] | Meeeee, M.; Meeeee, M.; Meeee, M.; Meeeeeeee, M. M.; Meeeeeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
[35] | Meee, M.; Meeeó, M., Meee. Mee., (8888) 888, 8888. |
[36] | Meeee, M. M.; Meeeeeeee, M., Meeeeeeeeee Meee., (8888), 8888. |
[37] | Meee, M.; Meeeeeeee, M. M.; Meeeee, M. M.; MeeMeeeeeeee, M.; MeMeeeee, M., M. Mee. Meeee. M: Meee., (8888) 888, 888. |
[38] | Meeee, M. M.; Meeeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[39] | Meeeeeee, M.; Meeeeeeee, M.; Meeeee, M.; Meeeeee, M., Meeeeeeeeeeeeee, (8888) 88, 8888. |
[40] | Meeeeeeee, M. M. M.; Meeeeee, M.; eee Meeee, M., Meee. Meee. Meee. Meee-Mee, (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 88-8, 888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.