Regio- and Diastereoselective Nickel-Catalyzed Allylation of Aromatic Aldehydes with α-Halo-β,β-difluoropropene Derivatives
Xiaowei Lin; Feng Zheng; Feng-Ling Qing; Journal of Organic Chemistry 77 (2012) 8696–8704; doi:10.1021/jo301688d

data_4027568
_publ_section_title
;
 Regio- and Diastereoselective Nickel-Catalyzed Allylation of Aromatic
 Aldehydes with \a-Halo-\b,\b-difluoropropene Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8696
_journal_page_last               8704
_journal_paper_doi               10.1021/jo301688d
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C19 H21 F O'
_chemical_formula_weight         284.36
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_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 106.523(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.679(2)
_cell_length_b                   5.3909(4)
_cell_length_c                   21.5262(16)
_cell_measurement_reflns_used    2770
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.709
_cell_measurement_theta_min      5.570
_cell_volume                     3190.6(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8641
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77957
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.148
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0648P)^2^+1.0149P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1292
_reflns_number_gt                2545
_reflns_number_total             3136
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301688d_si_002.cif
_cod_data_source_block           cd212119
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_cod_database_code               4027568