Synthesis of multisubstituted olefins through regio- and stereoselective silylborylation of an alkynylboronate/chemoselective cross-coupling sequences.
Jiao, Jiao; Nakajima, Kiyohiko; Nishihara, Yasushi; Organic letters 15 (2013) 3294–3297; doi:10.1021/ol401333j

data_1556192
_publ_section_title
;
 Synthesis of multisubstituted olefins through regio- and stereoselective
 silylborylation of an alkynylboronate/chemoselective cross-coupling
 sequences.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3294
_journal_page_last               3297
_journal_paper_doi               10.1021/ol401333j
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C29 H20 F3 N O'
_chemical_formula_sum            'C29 H20 F3 N O'
_chemical_formula_weight         455.46
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.885(15)
_cell_angle_beta                 86.412(13)
_cell_angle_gamma                78.391(17)
_cell_formula_units_Z            4
_cell_length_a                   10.299(4)
_cell_length_b                   12.070(6)
_cell_length_c                   19.582(6)
_cell_measurement_reflns_used    11130
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.00
_cell_volume                     2379.6(17)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_sigmaI/netI    0.1316
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21920
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_correction_T_min  0.9638
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         10725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.1988
_refine_ls_R_factor_gt           0.0759
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1155P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1889
_refine_ls_wR_factor_ref         0.2460
_reflns_number_gt                4020
_reflns_number_total             10725
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401333j_si_004.cif
_cod_data_source_block           yn26
_cod_original_cell_volume        2379.5(16)
_cod_database_code               1556192