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1.1.1.1 Hydroformylation of Linear Terminal Alkenes

DOI: 10.1055/sos-SD-212-00003

Bronger, R. P. J.; Kamer, P. C. J.; Vogt, D.Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (2014126.

Most often, oct-1-ene is used as a model substrate for linear alkenes and has been employed most extensively to test ligand effects in hydroformylation catalysis.[‌3‌] Many mono- and bidentate phosphines have been tested in the hydroformylation of oct-1-ene; a representative selection is presented in Table 1 (entries 1–10), as well as a few examples for the hydroformylation of hex-1-ene (entries 11–13).

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Meeee M8 Meeeee Meeee (°M) Meeeeeee (eee) Meeeee Meeeeeeee,e (%) Meeeeeeeeeeeee,e (%) Meeee Meeeeeeeeeee Meeeee (%) Mee
MM M8
8 (MM8)8Me Me8M 88 88 88 88.8 8.8 8888 8.8 88 [‌88‌]
8 (MM8)8Me 8 [M = (MM8)8] 88 88 88 88.8 8.8 88 8.8 88 [‌88‌]
8 (MM8)8Me 8 (M = MMe) 88 88 88 88.8 8.8 88 88.8 88 [‌88‌]
8 (MM8)8Me 8 (M = MeMe8) 88 88 88 88.8 8.8 88 88.8 88 [‌88‌]
8 (MM8)8Me 8 88 88 88 88.8 8.8 88 88.8 88 [‌88‌]
8 (MM8)8Me 8 (M = MMe8) 88 88 88 88.8 8.8 888 88.8 88 [‌88‌]
8 (MM8)8Me 8 (M = M=MMe8) 88 88 88 88.8 8.8 888 88.8 88 [‌88‌]
8 (MM8)8Me 8 (M = MM) 88 88 88 88.8 8.8 888 88.8 88 [‌88‌]
8 (MM8)8Me 8 (M = MMe) 88 88 88 88.8 8.8 888 88.8 88 [‌88‌]
88 (MM8)8Me 8 88 88 88 88.8 8.8 888 88.8 88 [‌88‌]
88 Me 8 88 8 8 e.e. e.e. 88 88.8 e.e. [‌88‌]
88 Me 8 88 8 8 e.e. e.e 8 88.8 e.e. [‌88‌]
88 Me 8 88 8 8 e.e. e.e. 8 8.8 e.e. [‌88‌]

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Meeee 8 Meeeeeeeeeeeeeee Meeee Meeeeee–Meeeeeeeeeeee Meeeeeeee[‌88‌,‌88‌‌88‌]

Meeee M8 M8 Meeeee Meeee (°M) Meeeeeee (eee) Meeeeeeeeeeeee (%) Meeee Meeeeeeeeeee Mee
MM M8
8 (MM8)8Me M M(MMe)8 88 8 8 e.e. 8.8 [‌88‌]
8 (MM8)8Me M (8-MeM8M8M)8M 88 8 8 e.e. 88.8 [‌88‌]
8 (MM8)8Me M (8-MeMM8M8M)8M 88 8 8 e.e. 8.8 [‌88‌]
8 (MM8)8Me M 8 88 88 88 88 88 888 8.8 [‌88‌‌88‌]
8 Me Me 8 88 8 8 8 8888 >888 [‌88‌]
8 Me 8 88 8 8 8 8888 >888 [‌88‌]

e Meeeeeeeee: [Me] = 8.8–8 eM, eeeee (eeeeee/Me) 88–88:8, [eeeeee] = 8.8–8 M ee eeeeeee ee eeeeeee.

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Meeee 8 eeeee eeeeeeeeeeeeeeee eeeee eee eeeeeeeeeeeee ee eeeeeeeeeeeeee eeeeeeeeeee-eeeee eeeeeeeee ee eee eeeeeeeeeeeeeeee ee eee-8-eee (eeeeeee 8–8 eee 8–88), eeeeeee (eeeeeee 8–8), eee eee-8-eee (eeeeeee 88–88).

Meeeee 8 Meeee Meeeeeeeeee Meeeeee eee Meeeeeeeeeeeeeee Meeeeeeee[‌88‌,‌88‌,‌88‌,‌88‌]

Meeee 8 Meeeeeeeeeeeeeee Meeee Meeeeee Meeeeeeee eeee Meeee Meeeeeeeeee Meeeeee[‌88‌,‌88‌,‌88‌,‌88‌]

Meeee M8 Meeeee Meeee (°M) MM/M8 Meeeeeee (eee) Meeee (MM/M8) Meeeeeeeeeeeee,e (%) Meeee,e Meeeeeeeeeee Mee
8 Me 88 88 8.8 8:8 e.e. 8888 88 [‌88‌,‌88‌]
8 Me 88 88 8.8 8:8 e.e. 888 88 [‌88‌,‌88‌]
8 Me 88 88 8 8:8 e.e. 8888 8.8 [‌88‌,‌88‌]
8 Me 88 88 8 8:8 e.e. 888 8.8 [‌88‌,‌88‌]
8 M 88 88 8.8 8:8 e.e. 888 8.8 [‌88‌,‌88‌]
8 M 88 88 8.8 8:8 e.e. 88 8.8 [‌88‌,‌88‌]
8 M 88 88 8.8 8:8 e.e. 888 88 [‌88‌,‌88‌]
8 Me 88 (e = 8) 88 8.8 8:8 e.e. 8888 8.8 [‌88‌,‌88‌]
8 Me 88 (e = 8) 88 8.8 8:8 e.e. 8888 8.8 [‌88‌,‌88‌]
88 Me 88 (e = 8) 88 8.8 8:8 e.e. 8888 8.8 [‌88‌,‌88‌]
88 Me 88 88 8.8 8:8 e.e. 8888 8.8 [‌88‌,‌88‌]
88 Me 88 88 8.8 8:8 e.e. 8888 8.8 [‌88‌,‌88‌]
88 (MM8)8Me 88 (e = 8) 88 88 8:8 e.e. 88 888 8.8 [‌88‌]
88 (MM8)8Me 88 (e = 8) 88 88 8:8 88 8888 8.8 [‌88‌]
88 (MM8)8Me 88 88 88 8:8 88 8888 >888 [‌88‌]
88 (MM8)8Me 88 88 88 8:8 88 8888 88 [‌88‌]
88 (MM8)8Me 88 88 88 8:8 e.e. 8888 88 [‌88‌]
88 (MM8)8Me 88 88 88 8:8 88 888 8.8 [‌88‌]
88 (MM8)8Me 88 888 88 8:8 e.e. e.e. 8 [‌88‌]
88 (MM8)8Me 88 888 88 8:8 e.e. e.e. 888 [‌88‌]

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Meeeeee (e.e., Meeee 8, Meeee 8); Meeeeee Meeeeeeee Meeee e Meeeeee–Meeeeeeeeeeeeeeeee Meeeeeee:[‌88‌]

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Meeeeeeeeeeeeeee eeeeeeeee eeee eeeeeee eee ee e eeee-eeee 888-eM eeeeeeeee eeeee eeeeeeeee eeeee eeeeeeeee ee eee. Mee-8-eee eee eeeeeee eeeeeeee eeeeeee e eeeee eeeeee ee eeeeeee eeeeeee (88–888 eeeeee, Meeee) ee eeeeee eeeeeeeeeeeeee.

Me e eeeeeee eeeeeeeeee eee eeeeeeeee eee eeeeee eeee e eeeeeee ee e 8 eM eeee ee Me(eeee)(MM)8 ee eeeeeee (8 eM, 8.888 eeee), Me8M (8.88 eeee), eee eeeeeee (88 eM) eeeee eeeee. Mee eeeeeeeee eee eeeeeeeeeee eeee eeeeee (MM/M8 8:8) ee 88 eee eee eee eeeeeeeeeee eee eeeeee ee 88 °M ee eeeeeeeeeeeee 88 eee. Meeeeeeeeeee, eee-8-eee (8.88 eM, 88 eeee) eee eeeeee (8.8 eM, 8 eeee) ee eeeeeeee eeeeeeee eeee eeeee eeeee eeeeeeee. Mee eeeeeee eeee eeeeeeee ee MM. Mee eeeeeeeeee, eeeeeeeeeeeee, eee eeeeee ee eeeeeeee eeeeee eeee eeeeeeeeee ee eee eeeeeeeeee eeeee eeeee eeee eeeeeeeee eee eee MMM eeeeee ee eee eeeeeee (888) eee M8-eeeeeeeee (888).

Meeeeee (e.e., Meeee 8, Meeee 8); Meeeeee Meeeeeeee Meeee e Meeeeee–Meeeeeee Meeeeeee:[‌88‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeee eee eeeeeee eeee ee eeeeeeeeeeeeeee eeee eeeeeeeeeee eeeeee eeeeeeeeeeee. Meeeeeee ee eeeeeeeee. Me eeeee ee eeeeeeeee eeee eee eeeeeeeee eeeeee ee eeee eee eeeeeeeeeeeeee. Meee eeeeeeeeeeeeee eeeee eeeeeeeeeee. Meee-eeeeeeee eeeeeeee eeeeee ee eeeeee ee eeeeeeee eeeeeeeeee eeeee eee eeeee eeeeeeeeeeeeee eeee eeeeee eeeeeeee eeeeee ee eeeeeeeee ee eeeeeee eeeeeeeee ee e eeeeee eeee. MM eee M8 eeeeeeeeeeeeee eeeeee ee eeeeeeeee ee eeeeee eeeeeeeee eeeeeeeee.

Meeeeeeeeeeeeeee eeeeeeeee eeee eeeeeee eee ee ee eeeeeeeee, eeeeeeee eeee e eeeee eeeee eeeeee, e eeeeeeeee-eeeee eeeeee, e eeeeee-eeeeeeee eeeee, eee e eeeeeeee eeeeeeee eee. Mee eeeeeeeeeee eee eeeeeeeeee ee ee eeeeeeeeee eeeeeee eeeeee. Me e eeeeeee eeeeeeeeee, Meeeeeee (8, M = MMe8; 88 µeee) eee eeeeee ee eee eeeeeeeee eee eee eeeeee eee eeeeeeeee eee eeeeee ee 88 °M. Meeee 8.8 e, eee eeeeeeeee eee eeeeee eeee MM/M8 (8:8) eee e eeee ee Me(eeee)(MM)8 (88 µeee) ee eeeeeee (8.8 eM). Mee eeeeeeeee eee eeeeeeeeeee ee 88 eee eee eeeeee ee 88 °M, eee eee eeeeeee eee eeeeeee eee 8.8 e ee eeee eee eeeeee eeeeeeee. Meee, eee-8-eee (8.8 eM; eeeeeeee eeeeeee eeeeeee eeeeeeeee eeeeeee ee eeeeee eeeeeeee eeeeeeeeee) eee eeeeeeee eeeeeeee eeeeee (8.8 eM) eeee eeeeee ee eee eeeeeeeee eeeeee, eeeee eee eeeeee eeee MM/M8 (8:8; 88 eee), eee eeeeeee eeee eee eeeeeeeee eeee MM/M8 (8:8; 88 eee). Me eee 88% eeeeeeeeee eeeee eee eeeeeeee eee eeeeeee ee eeeeee M(MMe)8 (8.88 eM) eee eee eeeeeee eee eeeeee ee eee. Meeeeee ee eee eeeeeee eeee eeeeeeee ee eeeeeeeeeee-eeeeeeeeee MM.

Meeeeeee (e.e., Meeee 8, Meeee 88); Meeeeee Meeeeeeee Meeee e Meeeeee–MMMMM Meeeeeee:[‌88‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeee eee eeeeeee eeee ee eeeeeeeeeeeeeee eeee eeeeeeeeeee eeeeee eeeeeeeeeeee. Meeeeeee ee eeeeeeeee. Me eeeee ee eeeeeeeee eeee eee eeeeeeeee eeeeee ee eeee eee eeeeeeeeeeeeee. Meee eeeeeeeeeeeeee eeeee eeeeeeeeeee. Meee-eeeeeeee eeeeeeee eeeeee ee eeeeee ee eeeeeeee eeeeeeeeee eeeee eee eeeee eeeeeeeeeeeeee eeee eeeeee eeeeeeee eeeeee ee eeeeeeeee ee eeeeeee eeeeeeeee ee e eeeeee eeee. MM eee M8 eeeeeeeeeeeeee eeeeee ee eeeeeeeee ee eeeeee eeeeeeeee eeeeeeeee.

Meeeeeeeeeeeeeee eeeeeeeee eeee eeeeeeeee ee e 88-eM Meeeee–Meeeee eeeeee eeeeeeee eeee e eee-eeeee eeeee, eeeeee-eeeeeeee eeeee, eee eeee-eeee eeeeeeee eeeeeee eee. Mee eeeeeeee eeeeeeeee eee eeeeeeee ee e eeeeeeee eeeeeeeeeee eeee eeeeeeeeee ee 88.8±8.8 °M ee e eeee-eeeeeeeeee eeee eeee. M eeeeeeee eeeeeee eeeeee eeeee eee eeee eeeeeeee eeeeeeeee eeeeeeee. Me(eeee)(MM)8 (8.8 ee, 8.888 eeee) eee MMMMM (8; 8.888 eeee) eeee eeeeee ee eee eeeeeeee eeeeeeeee eeeee M8. Mee eeeeee eee eeeeeee eeee 88 eeee ee MM/M8 eeeee eeeee eee eeee eeeeeeeeeee ee 8.8 eee eeee eeeeeeee MM/M8 (88.88% MM, 88.88% M8). Meeeeee (8.8 eM) (MMMMMMM: eeeeeeeeee) eee eeeeeee (eeeeeeee MM eeeeeeee; 8.88 eM, 8.8 eeee) eeee eeeee ee eeeeeeee eeeeeee ee eee eeeeeeeeeee eeeeee. Meeee eee eeeeeee eee eeee eeeeeee eee 8 e, eee-8-eee (8.88 eM, 88 eeee) eee eeeee. Mee eeeeeeee ee eee eeeeee eee eeeeeeeeee eeeeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeee MM/M8 eeeeeeeeeeee. Meeeeee eeee eeeeeee eee eee eeeeee-eeeeeeee eeeee eee eeeeeeee. Meeeeeee eee 8-eeeeeeeeeeeee eeee eeeeeeee ee eeeeeeeeeee-eeeeeeeeee MM ee ee MM8888M eeeeeeeeeeeee eeeeeeeeee ee e MM8888M eeeeeeeeee eeeee e 88 e × 8.88 ee eeeeee eeeeeeee eeeeeeeee eeeeee.

Meeeeee (e.e., Meeee 8, Meeee 8); Meeeeee Meeeeeeee Meeee Meeeeee–Meeeeeeee Meeeeeeee Meeeeeee:[‌88‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeee eee eeeeeee eeee ee eeeeeeeeeeeeeee eeee eeeeeeeeeee eeeeee eeeeeeeeeeee. Meeeeeee ee eeeeeeeee. Me eeeee ee eeeeeeeee eeee eee eeeeeeeee eeeeee ee eeee eee eeeeeeeeeeeeee. Meee eeeeeeeeeeeeee eeeee eeeeeeeeeee. Meee-eeeeeeee eeeeeeee eeeeee ee eeeeee ee eeeeeeee eeeeeeeeee eeeee eee eeeee eeeeeeeeeeeeee eeee eeeeee eeeeeeee eeeeee ee eeeeeeeee ee eeeeeee eeeeeeeee ee e eeeeee eeee. MM eee M8 eeeeeeeeeeeeee eeeeee ee eeeeeeeee ee eeeeee eeeeeeeee eeeeeeeee.

MMMMMMM: Meeeeeeee eeeeeeeee ee e eeee eeeeeeee eee eeeeeeeeee, eeee eeeeeeeeeeee eeeeeeeeee eeeeeeeeee.

M 8-M eeeeeeeee eee eeeeeee eeee eee-8-eee (888 e) ee eeeeeee (888 eM), M(MMe)8 (88 e), eee 8% Me/M (88 e) ee eee eeeeeee eeeeeeee [Me/M eee eeeeee eee eee eeee ee eeeeeeeeeee; ee eeeeeeeee eeeeeeeeeee eeeeeeee eeee ee MeM(MM)(MMe8)8 eeeee eee eeee eeeeee]. Mee eeeeeeeee eee eeeeee, eeeeee ee e eeeeeee eeeeee (Meeeeeee Meeeeeeeee Me.), eee eeeeeee eeee MM ee eeeeee eee eeeeeeeee eee. M8 eee MM eeee eeeee ee e 8:8 eeeee ee eeee eee eeeeeee eeeeeeee ee eeeeeeeeeeeee 8 eee. Meeeeee eee eeeeeee eee eeee eee eeeeeee, eee eee eeeeeeeeeee eee eeeeeeeeee ee eee eeeeeee eeeeeeeeeee ee 88 °M; eeeeeeee eeeee ee 88 °M ee eeee eeeee. Meee eee eeeeeeee eee eeeeeee ee eee eeeee eeeee ee eee eeeeeee eeeee (8 eee ee e 8.8–8 eee eeeeeeeeee), eeeeeee eee eeeeeee eeeee eeeee eeeeeeeee ee M8 eee MM eeee eeeee ee eeeeeeeeee eeeeeeee ee eeeee eee eeeee eeeeeeee eeeee. Meeeeee eee 8-eeeeeeeeeeeee eeee eeeeeeeee ee eeeeeeeeeeee ee e 88-ee eeeeeeee-eeee eeeeee. Mee eeeeee eeeeee eeeeeeeee ee 888 °M/88 Meee, eeeeeee eee eeeeeeee eeeeee(e) eeeeeeeee e eee eeeeeee eeeee eee eeee eeeeeee ee eee eeeeee eeee eeeee eeeeeeee. Mee eeeeee eeeeeeee eee eeeeeeeeeeeee ee eee eeeeeee 8M MMM eeeeeeeeee ee δ 8.88; eeeeeee eeee ee 8-eeeeeeeeeeeee eeeeee e eeeeeee ee δ 8.88 ee eeeeeeee ee eee eeeeeee.

Meeee-eeeee eeeeeeeeeeeeee eeeeeeee eeee eeeeeeeee eeee eee eee ee e Meeeee Meeeeeeee Meeeee 888 eeeeeeeeee. Mee eeeeee (8.88 ee. × 8 ee) eee eeeeee eeee 88% Meeeeeee 88M ee Mee Meeee M 88/88. Mee eeee eeeeeeeeeee eee 888 °M, eeeeeeeeee ee 888 °M eeeee eeeeeee ee eeeeeeeeeee. Meee eeee e eeeee eeeeeeeeeeeee; eee eeeeeeeeeeee eeee eeeee eee eeee, eeeee eee eeeeeeee eeeeeeeeeee ee eee eeee eee eee eeeeee eeeeeeee. Mee eeeee eeeeeeeee ee eee eeeeeeee eee eeeeee ee eeeeeeeeeeeee ee eee-8-eee ee eee-8-eee. Me e eeeeeee eeee eee eeeee ee eeeeeee eee 88%, ee 8-eeeeeeeeeeeee 88%, eee ee eee-8-eee 8%.

References